Aromatic amine derivative and electroluminescence device using the same

ABSTRACT

Provided are a novel aromatic amine derivative having a specific structure and an organic electroluminescence device in which an organic thin layer comprising a single layer or plural layers including a light emitting layer is interposed between a cathode and an anode, wherein at leas one layer of the above organic thin layer contains the aromatic amine derivative described above in the form of a single component or a mixed component. Thus, the organic electroluminescence device is less liable to be crystallized in molecules, improved in a yield in producing the organic electroluminescence device and extended in a lifetime.

CROSS-REFERENCE TO RELATED APPLICATIONS

The present application is a continuation of U.S. patent applicationSer. No. 14/838,414 filed Aug. 28, 2015, pending, which is acontinuation of U.S. patent application Ser. No. 14/093,892 filed Dec.2, 2013, U.S. Pat. No. 9,159,931, which is a continuation of U.S. patentapplication Ser. No. 13/360,513 filed Jan. 27, 2012, now U.S. Pat. No.8,623,522, which is a continuation-in-part of U.S. patent applicationSer. No. 11/696,514, filed on Apr. 4, 2007, now U.S. Pat. No. 8,129,038,which claims priority to Japanese patent application JP 2006-121672,filed on Apr. 26, 2006.

BACKGROUND OF THE INVENTION

The present invention relates to an aromatic amine derivative and anorganic electroluminescence (EL) device obtained by using the same, morespecifically to an organic EL device in which use of an aromatic aminederivative having a specific substituent for a hole transporting layerinhibits molecules from being crystallized to enhance a yield inproducing the organic EL device and improves a lifetime of the organicEL device and an aromatic amine derivative which materializes it.

RELATED ART

An organic EL device is a spontaneous light emitting device making useof the principle that a fluorescent substance emits light byrecombination energy of holes injected from an anode and electronsinjected from a cathode by applying an electric field. Since organic ELdevice of a laminate type driven at a low voltage was reported by C. W.Tang et al. of Eastman Kodak Company (C. W. Tang and S. A. Vanslyke,Applied Physics Letters, Vol. 51, p. 913, 1987), researches on organicEL devices comprising organic materials as structural materials haveactively been carried out. Tang et al. use tris(8-quinolinolato)aluminumfor the light emitting layer and a triphenyldiamine derivative for thehole transporting layer. The advantages of a laminate structure includean elevation in an efficiency of injecting holes into a light emittinglayer, a rise in a production efficiency of excitons produced byblocking electrons injected from a cathode to recombine them andshutting up of excitons produced in a light emitting layer. As shown inthe above example, a two-layer type comprising a hole transporting(injecting) layer and an electron transporting and light emitting layerand a three-layered type comprising a hole transporting (injecting)layer, a light emitting layer and an electron transporting (injecting)layer are well known as the device structures of an organic EL device.In such laminate type structural devices, device structures and formingmethods are studied in order to enhance a recombination efficiency ofholes and electrons injected.

Usually, when an organic EL device is operated and stored under hightemperature environment, brought about are adverse effects such as achange in a color of emitted light, a reduction in a current efficiency,a rise in an operating voltage and a reduction in an emission lifetime.A glass transition temperature (Tg) of a hole transporting material hasto be raised in order to prevent the above matters. Accordingly, thehole transporting material has to have a lot of aromatic groups in amolecule (for example, aromatic diamine derivatives described in Patentdocument 1 and aromatic fused ring diamine derivatives described inPatent document 2), and usually, structures having 8 to 12 benzene ringsare preferably used.

However, if they have a lot of aromatic groups in a molecule,crystallization is liable to be caused in forming a thin film using theabove hole transporting materials to produce an organic EL device, andproblems that an outlet of a crucible used for vapor deposition isclogged and that defects of a thin film originating in crystallizationare caused to bring about a reduction in a yield of an organic EL devicehave been brought about. Further, compounds having a lot of aromaticgroups in a molecule have usually a high glass transition temperature(Tg) but have a high sublimation temperature, and it is considered thatthe phenomena that decomposition is caused in vapor deposition and thata deposited film is unevenly formed are brought about, so that theproblem that the lifetime is short has been involved therein.

On the other hand, a publicly known document in which asymmetricaromatic amine derivatives are disclosed is available. For example,aromatic amine derivatives having an asymmetric structure are describedin Patent document 3, but no specific examples are found therein, andthe characteristics of the asymmetric compounds are not describedtherein at all. Further, the examples of asymmetric aromatic aminederivatives having phenanthrene are described in Patent document 4, butthey are handled on the same basis as symmetric compounds, and thecharacteristics of the asymmetric compounds are not described therein atall. Also, a specific synthetic process is required for the asymmetriccompounds, but descriptions on the production processes of theasymmetric compounds are not clearly shown in the above patents.Further, a production process of aromatic amine derivatives having anasymmetric structure is described in Patent document 5, but thecharacteristics of the asymmetric compound are not described therein.Thermally stable asymmetric compounds having a high glass transitiontemperature are described in Patent document 6, but only examples ofcompounds having carbazole are shown.

Further, compounds having dibenzofuran are reported in Patent documents7 to 13, but they assume a structure in which diamine compounds havedibenzofuran in a central skeleton thereof. Compounds havingdibenzofuran at a terminal are reported in Patent documents 14 to 15,but they are monoamine compounds. Only specific examples are shown inPatent documents 8 to 12. Actual examples are described in Patentdocuments 7 and 14, but they are used only as photoconductors. Anorganic EL device is described in Patent document 13, but it does nothave satisfactory performances.

As described above, organic EL devices having a long lifetime arereported, but they are not necessarily satisfactory. Accordingly,organic EL devices having more excellent performances are stronglyrequired to be developed.

Patent document 1: U.S. Pat. No. 4,720,432Patent document 2: U.S. Pat. No. 5,061,569Patent document 3: Japanese Patent Application Laid-Open No. 48656/1996Patent document 4: Japanese Patent Application Laid-Open No. 135261/1999Patent document 5: Japanese Patent Application Laid-Open No. 171366/2003Patent document 6: U.S. Pat. No. 6,242,115Patent document 7: Japanese Patent No. 2501198Patent document 8: Japanese Patent No. 2879370Patent document 9: Japanese Patent No. 3508984Patent document 10: Japanese Patent Application Laid-Open No. 34957/1993Patent document 11: Japanese Patent Application Laid-Open No.287408/1995Patent document 12: Japanese Patent No. 3114445Patent document 13: Japanese Patent Application Laid-Open No.112765/2005Patent document 14: Japanese Patent No. 3248627Patent document 15: Japanese Patent Application Laid-Open No.288462/2001

DISCLOSURE OF THE INVENTION

The present invention has been made in order to solve the problemsdescribed above, and an object thereof is to provide an organic ELdevice in which molecules are less liable to be crystallized and whichis improved in a yield in producing the organic EL device and has a longlifetime and an aromatic amine derivative which materializes it.

Intensive researches repeated by the present inventors in order toachieve the object described above have resulted in finding that theabove object can be achieved by using a novel aromatic amine derivativehaving a specific substituent represented by the following Formula (1)as a material for an organic EL device and using it particularly for ahole transporting layer, and thus the present inventors have come tocomplete the present invention.

Further, it has been found that an amino group substituted with an arylgroup having a furan structure represented by Formula (2) or Formula (3)is suited as an amine unit having the specific substituent. The aboveamine unit has a steric hindrance, so that interaction between themolecules is small, and therefore it has the effects thatcrystallization thereof is inhibited to enhance a yield in producing anorganic EL device and that the organic EL device obtained is extended ina lifetime. In particular, it has been found that a marked effect ofextending the lifetime is obtained by combining with a blue coloremitting device.

That is, the present invention provides an aromatic amine derivativerepresented by the following Formula (1):

wherein R₁ is a hydrogen atom, a substituted or non-substituted arylgroup having 5 to 50 ring carbon atoms, a substituted or non-substitutedalkyl group having 1 to 50 carbon atoms, a substituted ornon-substituted alkoxy group having 1 to 50 carbon atoms, a substitutedor non-substituted aralkyl group having 6 to 50 carbon atoms, asubstituted or non-substituted aryloxy group having 5 to 50 ring carbonatoms, a substituted or non-substituted arylthio group having 5 to 50ring carbon atoms, a substituted or non-substituted alkoxycarbonyl grouphaving 2 to 50 carbon atoms, an amino group substituted with asubstituted or non-substituted aryl group having 5 to 50 ring carbonatoms, a halogen atom, a cyano group, a nitro group, a hydroxyl group ora carboxyl group; a is an integer of 0 to 4, and b is an integer of 1 to3;plural R₁ may be combined with each other to form a cyclic structure ofa saturated or unsaturated five-membered ring or six-membered ring whichmay be substituted; at least one of Ar₁ to Ar₄ is represented by thefollowing Formula (2) or (3):

(wherein R₂ and R₃ each are selected independently from the same groupsas those of R₁ in Formula (1) described above;X is oxygen, sulfur, selenium or tellurium;c is an integer of 0 to 6; d is an integer of 0 to 3; and e is aninteger of 1 to 3;plural R₂ or R₃ may be combined with each other to form a cyclicstructure of a saturated or unsaturated five-membered ring orsix-membered ring which may be substituted;when e is 2 or more and d is not 0, plural R₃ may be combined with eachother to form a cyclic structure of a saturated or unsaturatedfive-membered ring or six-membered ring which may be substituted);

(wherein R₄ to R₆ each are selected independently from the same groupsas those of R₁ in Formula (1) described above;X is an oxygen or sulfur atom;f and h each are an integer of 0 to 4; g is an integer of 0 to 3; and iis an integer of 1 to 3;plural R₄ or R₅ or R₆ may be combined with each other to form a cyclicstructure of a saturated or unsaturated five-membered ring orsix-membered ring which may be substituted;when i is 2 or more and h is not 0, plural R₆ may be combined with eachother to form a cyclic structure of a saturated or unsaturatedfive-membered ring or six-membered ring which may be substituted);in Formula (1), among Ar₁ to Ar₄, the groups which are not representedby Formula (2) each are independently a substituted or non-substitutedaryl group having 6 to 50 ring carbon atoms or a substituted ornon-substituted aromatic heterocyclic group having 5 to 50 ring carbonatoms.

The present invention provides an aromatic amine derivative representedby the following Formula (5):

wherein at least one of Ar₇ to Ar₉ is represented by Formula (3)described above; in Formula (5), among Ar₁ to Ar₃, the groups which arenot represented by Formula (3) each are independently a hydrogen atom, asubstituted or non-substituted aryl group having 5 to 50 ring carbonatoms, a substituted or non-substituted alkyl group having 1 to 50carbon atoms, a substituted or non-substituted alkoxy group having 1 to50 carbon atoms, a substituted or non-substituted aralkyl group having 6to 50 carbon atoms, a substituted or non-substituted aryloxy grouphaving 5 to 50 ring carbon atoms, a substituted or non-substitutedarylthio group having 5 to 50 ring carbon atoms, a substituted ornon-substituted alkoxycarbonyl group having 2 to 50 carbon atoms, anamino group substituted with a substituted or non-substituted aryl grouphaving 5 to 50 ring carbon atoms, a halogen atom, a cyano group, a nitrogroup, a hydroxyl group or a carboxyl group.

Further, the present invention provides an organic EL device in which anorganic thin layer comprising a single layer or plural layers includinga light emitting layer is interposed between a cathode and an anode,wherein at leas one layer of the above organic thin layer contains thearomatic amine derivative described above in the form of a singlecomponent or a mixed component.

Effect of the Invention

The aromatic amine derivative of the present invention and the organicEL device obtained by using the same are less liable to be crystallizedin molecules, improved in a yield in producing the organic EL device andhave long lifetimes.

BEST MODE FOR CARRYING OUT THE INVENTION

The aromatic amine derivative of the present invention is represented bythe following Formula (1):

In Formula (1), R₁ is a hydrogen atom, a substituted or non-substitutedaryl group having 5 to 50 ring carbon atoms, a substituted ornon-substituted alkyl group having 1 to 50 carbon atoms, a substitutedor non-substituted alkoxy group having 1 to 50 carbon atoms, asubstituted or non-substituted aralkyl group having 6 to 50 carbonatoms, a substituted or non-substituted aryloxy group having 5 to 50ring carbon atoms, a substituted or non-substituted arylthio grouphaving 5 to 50 ring carbon atoms, a substituted or non-substitutedalkoxycarbonyl group having 2 to 50 carbon atoms, an amino groupsubstituted with a substituted or non-substituted aryl group having 5 to50 ring carbon atoms, a halogen atom, a cyano group, a nitro group, ahydroxyl group or a carboxyl group.

In Formula (1), at least one of Ar₁ to Ar₄ is represented by thefollowing Formula (2) or (3):

In Formula (2), R₂ and R₃ each are selected independently from the samegroups as those of R₁ in Formula (1) described above. X is oxygen,sulfur, selenium or tellurium, and it is preferably an oxygen or sulfuratom, more preferably an oxygen atom.

In Formula (3), R₄ to R₆ each are selected independently from the samegroups as those of R₁ in Formula (1) described above. X is oxygen,sulfur, selenium or tellurium, and it is an oxygen or sulfur atom,preferably an oxygen atom.

The aryl groups represented by R₁ to R₆ in Formulas (1) to (3) include,for example, phenyl, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl,9-anthryl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl,9-phenanthryl, 1-naphthacenyl, 2-naphthacenyl, 9-naphthacenyl,1-pyrenyl, 2-pyrenyl, 4-pyrenyl, 2-biphenylyl, 3-biphenylyl,4-biphenylyl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl,m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-tolyl, m-tolyl,p-tolyl, p-t-butylphenyl, p-(2-phenylpropyl)phenyl, 3-methyl-2-naphthyl,4-methyl-1-naphthyl, 4-methyl-1-anthryl, 4′-methylbiphenylyl,4″-t-butyl-p-terphenyl-4-yl, fluoranthenyl, fluorenyl, 1-pyrrolyl,2-pyrrolyl, 3-pyrrolyl, pyrazinyl, 2-pyridinyl, 3-pyridinyl,4-pyridinyl, 1-indolyl, 2-indolyl, 3-indolyl, 4-indolyl, 5-indolyl,6-indolyl, 7-indolyl, 1-isoindolyl, 2-isoindolyl, 3-isoindolyl,4-isoindolyl, 5-isoindolyl, 6-isoindolyl, 7-isoindolyl, 2-furyl,3-furyl, 2-benzofuranyl, 3-benzofuranyl, 4-benzofuranyl, 5-benzofuranyl,6-benzofuranyl, 7-benzofuranyl, 1-isobenzofuranyl, 3-isobenzofuranyl,4-isobenzofuranyl, 5-isobenzofuranyl, 6-isobenzofuranyl,7-isobenzofuranyl, quinolyl, 3-quinolyl, 4-quinolyl, 5-quinolyl,6-quinolyl, 7-quinolyl, 8-quinolyl, 1-isoquinolyl, 3-isoquinolyl,4-isoquinolyl, 5-isoquinolyl, 6-isoquinolyl, 7-isoquinolyl,8-isoquinolyl, 2-quinoxalinyl, 5-quinoxalinyl, 6-quinoxalinyl,1-carbazolyl, 2-carbazolyl, 3-carbazolyl, 4-carbazolyl, 9-carbazolyl,1-phenanthridinyl, 2-phenanthridinyl, 3-phenanthridinyl,4-phenanthridinyl, 6-phenanthridinyl, 7-phenanthridinyl,8-phenanthridinyl, 9-phenanthridinyl, 10-phenanthryldinyl, 1-acridinyl,2-acridinyl, 3-acridinyl, 4-acridinyl, 9-acridinyl,1,7-phenanthroline-2-yl, 1,7-phenanthroline-3-yl,1,7-phenanthroline-4-yl, 1,7-phenanthroline-5-yl,1,7-phenanthroline-6-yl, 1,7-phenanthroline-8-yl,1,7-phenanthroline-9-yl, 1,7-phenanthroline-10-yl,1,8-phenanthroline-2-yl, 1,8-phenanthroline-3-yl,1,8-phenanthroline-4-yl, 1,8-phenanthroline-5-yl,1,8-phenanthroline-6-yl, 1,8-phenanthroline-7-yl,1,8-phenanthroline-9-yl, 1,8-phenanthroline-10-yl,1,9-phenanthroline-2-yl, 1,9-phenanthroline-3-yl,1,9-phenanthroline-4-yl, 1,9-phenanthroline-5-yl,1,9-phenanthroline-6-yl, 1,9-phenanthroline-7-yl,1,9-phenanthroline-8-yl, 1,9-phenanthroline-10-yl,1,10-phenanthroline-2-yl, 1,10-phenanthroline-3-yl,1,10-phenanthroline-4-yl, 1,10-phenanthroline-5-yl,2,9-phenanthroline-1-yl, 2,9-phenanthroline-3-yl,2,9-phenanthroline-4-yl, 2,9-phenanthroline-5-yl,2,9-phenanthroline-6-yl, 2,9-phenanthroline-7-yl,2,9-phenanthroline-8-yl, 2,9-phenanthroline-10-yl,2,8-phenanthroline-1-yl, 2,8-phenanthroline-3-yl,2,8-phenanthroline-4-yl, 2,8-phenanthroline-5-yl,2,8-phenanthroline-6-yl, 2,8-phenanthroline-7-yl,2,8-phenanthroline-9-yl, 2,8-phenanthroline-10-yl,2,7-phenanthroline-1-yl, 2,7-phenanthroline-3-yl,2,7-phenanthroline-4-yl, 2,7-phenanthroline-5-yl,2,7-phenanthroline-6-yl, 2,7-phenanthroline-8-yl,2,7-phenanthroline-9-yl, 2,7-phenanthroline-10-yl, 1-phenazinyl,2-phenazinyl, 1-phenothiazinyl, 2-phenothiazinyl, 3-phenothiazinyl,4-phenothiazinyl, 10-phenothiazinyl, 1-phenoxazinyl, 2-phenoxazinyl,3-phenoxazinyl, 4-phenoxazinyl, 10-phenoxazinyl, 2-oxazolyl, 4-oxazolyl,5-oxazolyl, 2-oxadiazolyl, 5-oxadiazolyl, 3-furazanyl, 2-thienyl,3-thienyl, 2-methylpyrrole-1-yl, 2-methylpyrrole-3-yl,2-methylpyrrole-4-yl, 2-methylpyrrole-5-yl, 3-methylpyrrole-1-yl,3-methylpyrrole-2-yl, 3-methylpyrrole-4-yl, 3-methylpyrrole-5-yl,2-t-butylpyrrole-4-yl, 3-(2-phenylpropyl)pyrrole-1-yl,2-methyl-1-indolyl, 4-methyl-1-indolyl, 2-methyl-3-indolyl,4-methyl-3-indolyl, 2-t-butyl-1-indolyl, 4-t-butyl-1-indolyl,2-t-butyl-3-indolyl and 4-t-butyl-3-indolyl.

Among them, preferred are phenyl, naphthyl, biphenyl, anthranyl,phenanthryl, pyrenyl, chrysenyl, fluoranthenyl and fluorenyl.

The alkyl groups represented by R₁ to R₆ in Formulas (1) to (3) include,for example, methyl, ethyl, propyl, isopropyl, n-butyl, s-butyl,isobutyl, t-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, hydroxymethyl,1-hydroxyethyl, 2-hydroxyethyl, 2-hydroxyisobutyl, 1,2-dihydroxyethyl,1,3-dihydroxyisopropyl, 2,3-dihydroxy-t-butyl, 1,2,3-trihydroxypropyl,chloromethyl, 1-chloroethyl, 2-chloroethyl, 2-chloroisobutyl,1,2-dichloroethyl, 1,3-dichloroisopropyl, 2,3-dichloro-t-butyl,1,2,3-trichloropropyl, bromomethyl, 1-bromoethyl, 2-bromoethyl,2-bromoisobutyl, 1,2-dibromoethyl, 1,3-dibromoisopropyl,2,3-dibromo-t-butyl, 1,2,3-tribromopropyl, iodomethyl, 1-iodoethyl,2-iodoethyl, 2-iodoisobutyl, 1,2-diiodoethyl, 1,3-diiodoisopropyl,2,3-diiodo-t-butyl, 1,2,3-triiodopropyl, aminomethyl, 1-aminoethyl,2-aminoethyl, 2-aminoisobutyl, 1,2-diaminoethyl, 1,3-diaminoisopropyl,2,3-diamino-t-butyl, 1,2,3-triaminopropyl, cyanomethyl, 1-cyanoethyl,2-cyanoethyl, 2-cyanoisobutyl, 1,2-dicyanoethyl, 1,3-dicyanoisopropyl,2,3-dicyano-t-butyl, 1,2,3-tricyanopropyl, nitromethyl, 1-nitroethyl,2-nitroethyl, 2-nitroisobutyl, 1,2-dinitroethyl, 1,3-dinitroisopropyl,2,3-dinitro-t-butyl, 1,2,3-trinitropropyl, cyclopropyl, cyclobutyl,cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 1-adamantyl, 2-adamantyl,1-norbornyl and 2-norbornyl.

The alkoxy groups represented by R₁ to R₆ in Formulas (1) to (3) aregroups represented by —OY, and the examples of Y include the sameexamples as explained in the alkyl group described above.

The aralkyl groups represented by R₁ to R₆ in Formulas (1) to (3)include, for example, benzyl, 1-phenyl ethyl, 2-phenylethyl,1-phenylisopropyl, 2-phenylisopropyl, phenyl-t-butyl, α-naphthylmethyl,1-α-naphthylethyl, 2-α-naphthylethyl, 1-α-naphthylisopropyl,2-α-naphthylisopropyl, β-naphthylmethyl, 1-β-naphthylethyl,2-β-naphthylethyl, 1-β-naphthylisopropyl, 2-β-naphthylisopropyl,1-pyrrolylmethyl, 2-(1-pyrrolyl)ethyl, p-methylbenzyl, m-methylbenzyl,o-methylbenzyl, p-chlorobenzyl, m-chlorobenzyl, o-chlorobenzyl,p-bromobenzyl, m-bromobenzyl, o-bromobenzyl, p-iodobenzyl, m-iodobenzyl,o-iodobenzyl, p-hydroxybenzyl, m-hydroxybenzyl, o-hydroxybenzyl,p-aminobenzyl, m-aminobenzyl, o-aminobenzyl, p-nitrobenzyl,m-nitrobenzyl, o-nitrobenzyl, p-cyanobenzyl, m-cyanobenzyl,o-cyanobenzyl, 1-hydroxy-2-phenylisopropyl and1-chloro-2-phenylisopropyl.

The aryloxy groups represented by R₁ to R₆ in Formulas (1) to (3) arerepresented by —OY′, and the examples of Y′ include the same examples asexplained in the aryl group described above.

The arylthio groups represented by R₁ to R₆ in Formulas (1) to (3) arerepresented by —SY′, and the examples of Y′ include the same examples asexplained in the aryl group described above.

The alkoxycarbonyl groups represented by R₁ to R₆ in Formulas (1) to (3)are represented by —COOY, and the examples of Y include the sameexamples as explained in the alkyl group described above.

The examples of the aryl group in the amino group substituted with thearyl group represented by R₁ to R₆ in Formulas (1) to (3) include thesame examples as explained in the aryl group described above.

The halogen atoms represented by R₁ to R₆ in Formulas (1) to (3) includea fluorine atom, a chlorine atom, a bromine atom and an iodine atom.

In Formula (1), a is an integer of 0 to 4, and b is an integer of 1 to3, preferably 2. Plural R₁ may be combined with each other to form acyclic structure of a saturated or unsaturated five-membered ring orsix-membered ring which may be substituted.

In Formula (2), c is an integer of 0 to 6; d is an integer of 0 to 3;and e is an integer of 1 to 3, preferably 1. Plural R₂ or R₃ may becombined with each other to form a cyclic structure of a saturated orunsaturated five-membered ring or six-membered ring which may besubstituted. When e is 2 or more and d is not 0, plural R₃ may becombined with each other to form a cyclic structure of a saturated orunsaturated five-membered ring or six-membered ring which may besubstituted.

In Formula (3), f and h each are an integer of 0 to 4; g is an integerof 0 to 3; and i is an integer of 1 to 3, preferably 1. Plural R₄ or R₅or R₆ may be combined with each other to form a cyclic structure of asaturated or unsaturated five-membered ring or six-membered ring whichmay be substituted. When i is 2 or more and h is not 0, plural R₆ may becombined with each other to form a cyclic structure of a saturated orunsaturated five-membered ring or six-membered ring which may besubstituted.

The above cyclic structure of a five-membered ring or a six-memberedring which may be formed includes, for example, cycloalkanes having 4 to12 carbon atoms such as cyclopentane, cyclohexane, adamantane,norbornane and the like, cycloalkenes having 4 to 12 carbon atoms suchas cyclopentene, cyclohexene and the like, cycloalkadienes having 6 to12 carbon atoms such as cyclopentadiene, cyclohexadiene and the like andaromatic rings having 6 to 50 carbon atoms such as benzene, naphthalene,phenanthrene, anthracene, pyrene, chrysene, acenaphthylene and the like.

The aromatic amine derivative of the present invention represented byFormula (1) has 42 or more carbon atoms, preferably 54 or more carbonatoms and more preferably 60 to 80 carbon atoms in terms of the total ofcarbon atoms excluding those of the substituents.

In the aromatic amine derivative of the present invention, Ar₁ and Ar₂in Formula (1) described above are represented preferably by Formula (2)or Formula (3) described above.

In the aromatic amine derivative of the present invention, Ar₁ and Ar₃in Formula (1) described above are represented preferably by Formula (2)or Formula (3) described above.

In the aromatic amine derivative of the present invention, only Ar₁ inFormula (1) described above is represented preferably by Formula (2) orFormula (3) described above.

In the aromatic amine derivative of the present invention, b in Formula(1) described above is preferably 2.

In the aromatic amine derivative of the present invention, f in Formula(2) described above is preferably 1.

In the aromatic amine derivative of the present invention, i in Formula(3) described above is preferably 1.

In the aromatic amine derivative of the present invention, X in Formula(2) described above is preferably an oxygen atom.

In the aromatic amine derivative of the present invention, Ar₂ inFormula (1) described above is represented preferably by the followingFormula (4):

In Formula (4), R₇ is selected from the same groups as those of R₁ inFormula (1) described above, and the specific examples thereof includeas well the same groups as the examples of R₁ to R₆ in Formulas (1) to(3).

In Formula (4), j is an integer of 0 to 4; and k is an integer of 1 to3. Plural R₇ may be combined with each other to form a cyclic structureof a saturated or unsaturated five-membered ring or six-membered ringwhich may be substituted. When k is 2 or more and j is not 0, plural R₇may be combined with each other to form a cyclic structure of asaturated or unsaturated five-membered ring or six-membered ring whichmay be substituted. In the above case, the specific examples of thecyclic structure of a five-membered ring or a six-membered ring includeas well the same ones as the examples of R₁ to R₆.

Ar₆ and Ar₇ each are independently a substituted or non-substituted arylgroup having 6 to 50 ring carbon atoms or a substituted ornon-substituted aromatic heterocyclic group having 5 to 50 ring carbonatoms. The specific examples of the above aryl group or aromaticheterocyclic group include the same groups as the examples of the arylgroups represented by R₁ to R₆.

In the aromatic amine derivative of the present invention, Ar₂ and Ar₄in Formula (1) described above each are preferably representedindependently by Formula (4) described above.

The aromatic amine derivative of the present invention is represented bythe following Formula (5):

In Formula (5), at least one of Ar₇ to Ar₉ is represented by Formula (3)described above, and among Ar₁ to Ar₃, the groups which are notrepresented by Formula (3) each are independently a hydrogen atom, asubstituted or non-substituted aryl group having 5 to 50 ring carbonatoms, a substituted or non-substituted alkyl group having 1 to 50carbon atoms, a substituted or non-substituted alkoxy group having 1 to50 carbon atoms, a substituted or non-substituted aralkyl group having 6to 50 carbon atoms, a substituted or non-substituted aryloxy grouphaving 5 to 50 ring carbon atoms, a substituted or non-substitutedarylthio group having 5 to 50 ring carbon atoms, a substituted ornon-substituted alkoxycarbonyl group having 2 to 50 carbon atoms, anamino group substituted with a substituted or non-substituted aryl grouphaving 5 to 50 ring carbon atoms, a halogen atom, a cyano group, a nitrogroup, a hydroxyl group or a carboxyl group. The specific examplesthereof include as well the same groups as the examples of R₁ to R₆.

The aromatic amine derivative of the present invention is preferably amaterial for an organic electroluminescence device.

The aromatic amine derivative of the present invention is preferably ahole transporting material for an organic electroluminescence device.

The aromatic amine derivative of the present invention is preferably ahole injecting material for an organic electroluminescence device.

The aromatic amine derivative of the present invention is preferably amaterial having the functions of a hole injecting material and a holetransporting material for an organic electroluminescence device incombination.

In the organic electroluminescence device of the present invention inwhich an organic thin layer comprising a single layer or plural layersincluding at leas a light emitting layer is interposed between a cathodeand an anode, at leas one layer of the above organic thin layer containspreferably the aromatic amine derivative of the present inventiondescribed above in the form of a single component or a mixed component.

In the organic electroluminescence device of the present invention, thearomatic amine derivative of the present invention described above iscontained preferably in a hole transporting layer.

In the organic electroluminescence device of the present invention, thearomatic amine derivative of the present invention described above iscontained preferably in a hole injecting layer.

In the organic electroluminescence device of the present invention,styrylamine and/or arylamine are contained preferably in a lightemitting layer.

In the organic electroluminescence device of the present invention,light of a blue color is preferably emitted.

The specific examples of the aromatic amine derivative of the presentinvention represented by Formula (1) are shown below, but they shall notbe restricted to these compounds shown as the examples.

Next, the organic EL device of the present invention shall be explained.

In the organic EL device of the present invention in which an organicthin film layer comprising a single layer or plural layers including atleast a light emitting layer is interposed between a cathode and ananode, at least one layer of the above organic thin film layer containsthe aromatic amine derivative described above in the form of a singlecomponent or a mixed component.

In the organic EL device of the present invention, the organic thin filmlayer described above has a hole transporting layer, and the above holetransporting layer contains preferably the aromatic amine derivative ofthe present invention in the form of a single component or a mixedcomponent. Further, the hole transporting layer described above containsmore preferably the aromatic amine derivative of the present inventionas a principal component.

The aromatic amine derivative of the present invention is usedpreferably for an organic EL device emitting light of a blue color base.

The organic electroluminescence device of the present invention containspreferably a styrylamine compound and/or an arylamine compound in alight emitting layer.

The arylamine compound includes a compound represented by the followingFormula (1), and the styrylamine compound includes a compoundrepresented by the following Formula (II):

(in Formula (1), Ar₈ is a group selected from phenyl, biphenyl,terphenyl, stilbene and distyrylaryl; Ar₉ and Ar₁₀ each are a hydrogenatom or an aromatic group having 6 to 20 carbon atoms, and Ar₉ and Ar₁₀may be substituted; p′ is an integer of 1 to 4; and Ar₉ and/or Ar₁₀ aremore preferably substituted with a styryl group).

In this regard, the aromatic group having 6 to 20 carbon atoms includespreferably phenyl, naphthyl, anthranyl, phenanthryl, terphenyl and thelike.

(in Formula (II), Ar₁₁ to Ar₁₃ are an aryl group having 5 to 40 ringcarbon atoms which may be substituted, and is an integer of 1 to 4).

In this regard, the aryl group having 5 to 40 ring carbon atoms includespreferably phenyl, naphthyl, anthranyl, phenanthryl, pyrenyl, coronyl,biphenyl, terphenyl, pyrrolyl, furanyl, thiophenyl, benzothiophenyl,oxadiazolyl, diphenylanthranyl, indolyl, carbazolyl, pyridyl,benzoquinolyl, fluoranthenyl, acenaphthofluoranthenyl, stilbene and thelike. The aryl group having 5 to 40 ring carbon atoms may further besubstituted with a substituent, and the preferred substituent includesan alkyl group having 1 to 6 carbon atoms (ethyl, methyl, i-propyl,n-propyl, s-butyl, t-butyl, pentyl, hexyl, cyclopentyl, cyclohexyl andthe like), an alkoxy group having 1 to 6 carbon atoms (ethoxy, methoxy,i-propoxy, n-propoxy, s-butoxy, t-butoxy, pentoxy, hexyloxy,cyclopentoxy, cyclohexyloxy and the like), an aryl group having 5 to 40ring carbon atoms, an amino group substituted with an aryl group having5 to 40 ring carbon atoms, an ester group having an aryl group having 5to 40 ring carbon atoms, an ester group having an alkyl group having 1to 6 carbon atoms, a cyano group, a nitro group and a halogen atom(chlorine, bromine, iodine and the like).

The device structure of the organic EL device of the present inventionshall be explained below.

(1) Structure of the Organic EL Element

The typical examples of the device structure of the organic EL device ofthe present invention include structures such as:

-   -   (1) Anode/light emitting layer/cathode    -   (2) Anode/hole injecting layer/light emitting layer/cathode    -   (3) Anode/light emitting layer/electron injecting layer/cathode    -   (4) Anode/hole injecting layer/light emitting layer/electron        injecting layer/cathode    -   (5) Anode/organic semiconductor layer/light emitting        layer/cathode    -   (6) Anode/organic semiconductor layer/electron barrier        layer/light emitting layer/cathode    -   (7) Anode/organic semiconductor layer/light emitting        layer/adhesion improving layer/cathode    -   (8) Anode/hole injecting layer/hole transporting layer/light        emitting layer/electron injecting layer/cathode    -   (9) Anode/insulating layer/light emitting layer/insulating        layer/cathode    -   (10) Anode/inorganic semiconductor layer/insulating layer/light        emitting layer/insulating layer/cathode    -   (11) Anode/organic semiconductor layer/insulating layer/light        emitting layer/insulating layer/cathode    -   (12) Anode/insulating layer/hole injecting layer/hole        transporting layer/light emitting layer/insulating layer/cathode    -   (13) Anode/insulating layer/hole injecting layer/hole        transporting layer/light emitting layer/electron injecting        layer/cathode

Among them, usually the structure of (8) is preferably used, but itshall not be restricted to them.

The aromatic amine derivative of the present invention may be used inany organic thin film layer of the organic EL device and can be used inthe light emitting zone or the hole transporting zone, and it is usedpreferably in the hole transporting zone, particularly preferably in thehole transporting layer, whereby the molecules are less liable to becrystallized, and a yield in producing the organic EL device iselevated.

An amount of the aromatic amine derivative of the present inventionwhich is added to the organic thin film layer is preferably 30 to 100mole %.

(2) Light Transmitting Substrate

The organic EL device of the present invention is prepared on a lighttransmitting substrate. The light transmitting substrate referred to inthis case is a substrate for supporting the organic EL device, and it ispreferably a flat substrate in which light in a visible region of 400 to700 nm has a transmission factor of 50% or more.

To be specific, it includes a glass plate, a polymer plate and the like.In particular, the glass plate includes soda lime glass,barium.cndot.strontium-containing glass, lead glass, aluminosilicateglass, borosilicate glass, barium borosilicate glass, quartz and thelike. The polymer plate includes polycarbonate, acryl, polyethyleneterephthalate, polyether sulfide, polysulfone and the like.

(3) Anode

An anode in the organic EL device of the present invention has afunction to inject a hole into the hole transporting layer or the lightemitting layer, and it is effective that the anode has a work functionof 4.5 eV or more. The specific examples of a material for the anodeused in the present invention include indium tin oxide alloy (ITO), zincoxide (NESA), indium-zinc oxide (IZO), gold, silver, platinum, copperand the like.

The anode can be prepared by forming a thin film of the above electrodesubstances by a method such as a vapor deposition method, a sputteringmethod and the like.

When light emitted from the light emitting layer is taken out from theanode, a transmission factor of the anode based on light emitted ispreferably larger than 10%. A sheet resistance of the anode ispreferably several hundred Ω/□ or less. A film thickness of the anode isselected, though depending on the material, in a range of usually 10 nmto 1 μm, preferably 10 to 200 nm.

(4) Light Emitting Layer

The light emitting layer in the organic EL device has the followingfunctions of (1) to (3) in combination.

-   -   (1) Injecting function: a function in which a hole can be        injected from an anode or a hole injecting layer in applying an        electric field and in which an electron can be injected from a        cathode or an electron injecting layer.    -   (2) Transporting function: a function in which a charge injected        (electron and hole) is transferred by virtue of a force of an        electric field.    -   (3) Light emitting function: a function in which a field for        recombination of an electron and a hole is provided and in which        this is connected to light emission.

Provided that a difference between an easiness in injection of a holeand an easiness in injection of an electron may be present and that adifference may be present in a transporting ability shown by themobilities of a hole and an electron, and any one of the charges ispreferably transferred.

A publicly known method such as, for example, a vapor deposition method,a spin coating method, an LB method and the like can be applied as amethod for forming the above light emitting layer. In particular, thelight emitting layer is preferably a molecular deposit film. In thiscase, the molecular deposit film means a thin film formed by depositinga material compound staying in a gas phase state and a film formed bysolidifying a material compound staying in a solution state or a liquidphase state, and the above molecular deposit film can usually bedistinguished from a thin film formed by the LB method (molecularaccumulation film) by a difference in an aggregation structure and ahigher order structure and a functional difference originating in it.

Further, as disclosed in Japanese Patent Application Laid-Open No.51781/1982, the light emitting layer can be formed as well by dissolvinga binding agent such as a resin and the material compound in a solventto prepare a solution and then coating the solution by a spin coatingmethod and the like to form a thin film.

In the present invention, publicly known light emitting materials otherthan the light emitting material comprising the aromatic aminederivative of the present invention may be added, if necessary, to thelight emitting layer as long as the object of the present invention isnot damaged. Further, a light emitting layer containing a differentpublicly known light emitting material may be laminated on the lightemitting layer containing the light emitting material comprising thearomatic amine derivative of the present invention.

A luminescent material or a doping material which can be used for thelight emitting layer together with the aromatic amine compound of thepresent invention includes, for example, anthracene, naphthalene,phenanthrene, pyrene, tetracene, coronene, chrysene, fluorescein,perylene, phthaloperylene, naphthaloperylene, perynone, phthaloperynone,naphthaloperynone, diphenylbutadiene, tetraphenylbutadiene, coumarin,oxadiazole, aldazine, bisbenzoxazoline, bisstyryl, pyrazine,cyclopentadiene, quinoline metal complexes, aminoquinoline metalcomplexes, benzoquinoline metal complexes, imine, diphenylethylene,vinylanthracene, diaminocarbazole, pyran, thiopyran, polymethine,merocyanine, imidazole chelated oxynoid compounds, quinacridone,rubrene, fluorescent coloring matters and the like. However, it shallnot be restricted to them.

The host material which can be used for the light emitting layertogether with the aromatic amine compound of the present invention ispreferably compounds represented by the following Formulas (i) to (ix).

Asymmetric anthracene compound represented by the following Formula (1):

wherein Ar is a substituted or non-substituted fused aromatic grouphaving 10 to 50 ring carbon atoms;Ar′ is a substituted or non-substituted aromatic group having 6 to 50ring carbon atoms;X is a substituted or non-substituted aromatic group having 6 to 50 ringcarbon atoms, a substituted or non-substituted aromatic heterocyclicgroup having 5 to 50 ring carbon atoms, a substituted or non-substitutedalkyl group having 1 to 50 carbon atoms, a substituted ornon-substituted alkoxy group having 1 to 50 carbon atoms, a substitutedor non-substituted aralkyl group having 6 to 50 carbon atoms, asubstituted or non-substituted aryloxy group having 5 to 50 ring carbonatoms, a substituted or non-substituted arylthio group having 5 to 50ring carbon atoms, a substituted or non-substituted alkoxycarbonyl grouphaving 1 to 50 ring carbon atoms, a carboxyl group, a halogen atom, acyano group, a nitro group or a hydroxyl group;a, b and c each are an integer of 0 to 4;n is an integer of 1 to 3; and when n is 2 or more, an inside ofbrackets may be the same or different.

Asymmetric monoanthracene derivative represented by the followingFormula (ii):

wherein Ar¹ and Ar² each are independently a substituted ornon-substituted aromatic ring group having 6 to 50 ring carbon atoms; mand n each are an integer of 1 to 4; provided that when m and n are 1and the positions of Ar¹ and Ar² bonded to the benzene ring arebilaterally symmetric, Ar¹ and Ar² are not the same, and when m and nare an integer of 2 to 4, m and n are different integers; and R¹ to R¹⁰each are independently a hydrogen atom, a substituted or non-substitutedaromatic ring group having 6 to 50 ring carbon atoms, a substituted ornon-substituted aromatic heterocyclic group having 5 to 50 ring carbonatoms, a substituted or non-substituted alkyl group having 1 to 50carbon atoms, a substituted or non-substituted cycloalkyl group, asubstituted or non-substituted alkoxy group having 1 to 50 carbon atoms,a substituted or non-substituted aralkyl group having 6 to 50 carbonatoms, a substituted or non-substituted aryloxy group having 5 to 50ring carbon atoms, a substituted or non-substituted arylthio grouphaving 5 to 50 ring carbon atoms, a substituted or non-substitutedalkoxycarbonyl group having 1 to 50 ring carbon atoms, a substituted ornon-substituted silyl group, a carboxyl group, a halogen atom, a cyanogroup, a nitro group or a hydroxyl group.

Asymmetric pyrene derivative represented by the following Formula (iii):

wherein Ar and Ar′ each are a substituted or non-substituted aromaticgroup having 6 to 50 ring carbon atoms;L and L′ each are a substituted or non-substituted phenylene group, asubstituted or non-substituted naphthalenylene group, a substituted ornon-substituted fluorenylene group or a substituted or non-substituteddibenzosilolylene group;m is an integer of 0 to 2; n is an integer of 1 to 4; s is an integer of0 to 2; and t is an integer of 0 to 4;L or Ar is bonded to any of 1- to 5-positions of pyrene, and L′ or Ar′is bonded to any of 6- to 10-positions of pyrene;provided that when n+t is an even number, Ar, Ar′, L and L′ satisfy (1)or (2) described below:(1) Ar≠Ar′ and/or L≠L′ (in this case, ≠ shows that both are groupshaving different structures) and(2) when Ar=Ar′ and L=L′,

(2-1) m≠s and/or nit or

(2-2) when m=s and/or n=t,

there are not a case in which (2-2-1) L and L′ or pyrene each are bondedto different bonding positions on Ar and Ar′ or (2-2-2) L and L′ orpyrene are bonded to the same bonding position on Ar and Ar′ and a casein which the substitution positions of L and L′ or Ar and Ar′ in pyreneare a 1-position and a 6-position or a 2-position and a 7-position.

Asymmetric anthracene derivative represented by the following Formula(Iv):

wherein A¹ and A² each are independently a substituted ornon-substituted fused aromatic group having 10 to 20 ring carbon atoms;Ar¹ and Ar² each are independently a hydrogen atom or a substituted ornon-substituted aromatic ring group having 6 to 50 ring carbon atoms;R¹ to R¹⁰ each are independently a hydrogen atom, a substituted ornon-substituted aromatic ring group having 6 to 50 ring carbon ringatoms, a substituted or non-substituted aromatic heterocyclic grouphaving 5 to 50 ring carbon atoms, a substituted or non-substituted alkylgroup having 1 to 50 carbon atoms, a substituted or non-substitutedcycloalkyl group, a substituted or non-substituted alkoxy group having 1to 50 carbon atoms, a substituted or non-substituted aralkyl grouphaving 6 to 50 carbon atoms, a substituted or non-substituted aryloxygroup having 5 to 50 ring carbon atoms, a substituted or non-substitutedarylthio group having 5 to 50 ring carbon atoms, a substituted ornon-substituted alkoxycarbonyl group having 1 to 50 ring carbon atoms, asubstituted or non-substituted silyl group, a carboxyl group, a halogenatom, a cyano group, a nitro group or a hydroxyl group; Ar¹, Ar², R⁹ andR¹⁰ each may be plural, and adjacent ones may form a saturated orunsaturated cyclic structure;provided that there is no case in which in Formula (1), groups symmetricto an X-Y axis shown on the above anthracene are bonded to a 9-positionand a 10-position of central anthracene.

Anthracene derivative represented by the following Formula (v):

wherein R¹ to R¹⁰ each represent independently a hydrogen atom, an alkylgroup, a cycloalkyl group, an aryl group which may be substituted, analkoxyl group, an aryloxy group, an alkylamino group, an alkenyl group,an arylamino group or a heterocyclic group which may be substituted; aand b each represent an integer of 1 to 5; when they are 2 or more, R¹'sthemselves or R²'s themselves each may be the same as or different fromeach other, and R¹'s themselves or R²'s themselves may be combined witheach other to form a ring; R³ and R⁴, R⁵ and R⁶, R⁷ and R⁸ and R⁹ andR¹⁰ may be combined with each other to form rings; and L¹ represents asingle bond, —O—, —S—, —N(R)— (R is an alkyl group or an aryl groupwhich may be substituted), an alkylene group or an arylene group.

Anthracene derivative represented by the following Formula (vi):

wherein R¹¹ to R²⁰ each represent independently a hydrogen atom, analkyl group, a cycloalkyl group, an aryl group, an alkoxyl group, anaryloxy group, an alkylamino group, an arylamino group or a heterocyclicgroup which may be substituted; c, d, e and f each represent an integerof 1 to 5; when they are 2 or more, R¹¹'s themselves, R¹²'s themselves,R¹⁶'s themselves or R¹⁷'s themselves may be the same as or differentfrom each other, and R¹¹'s themselves, R¹²'s themselves, R¹⁸'sthemselves or R¹⁷'s themselves may be combined with each other to form aring; R′3 and R¹⁴ and R¹⁸ and R¹⁹ may be combined with each other toform rings; and L² represents a single bond, —O—, —S—, —N(R)— (R is analkyl group or an aryl group which may be substituted), an alkylenegroup or an arylene group.

Spirofluorene derivative represented by the following Formula (vii):

wherein A⁵ to A⁸ each are independently a substituted or non-substitutedbiphenyl group or a substituted or non-substituted naphthyl group.

Fused ring-containing compound represented by the following Formula(viii):

wherein A⁹ to A¹⁴ are the same as those described above; R²¹ to R²³ eachrepresent independently a hydrogen atom, an alkyl group having 1 to 6carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, an alkoxylgroup having 1 to 6 carbon atoms, an aryloxy group having 5 to 18 carbonatoms, an aralkyloxy group having 7 to 18 carbon atoms, an arylaminogroup having 5 to 16 carbon atoms, a nitro group, a cyano group, anester group having 1 to 6 carbon atoms or a halogen atom; and at leastone of A⁹ to A¹⁴ is a group having 3 or more fused aromatic rings.

Fluorene compound represented by the following Formula (ix):

wherein R₁ and R₂ represent a hydrogen atom, a substituted ornon-substituted alkyl group, a substituted or non-substituted aralkylgroup, a substituted or non-substituted aryl group, a substituted ornon-substituted heterocyclic group, a substituted amino group, a cyanogroup or a halogen atom; R₁'s themselves and R₂'s themselves which arebonded to the different fluorene groups may be the same as or differentfrom each other, and R₁ and R₂ which are bonded to the same fluorenegroup may be the same as or different from each other; R₃ and R₄represent a hydrogen atom, a substituted or non-substituted alkyl group,a substituted or non-substituted aralkyl group, a substituted ornon-substituted aryl group or a substituted or non-substitutedheterocyclic group; R₃'s themselves and R₄'s themselves which are bondedto the different fluorene groups may be the same as or different fromeach other, and R₃ and R₄ which are bonded to the same fluorene groupmay be the same as or different from each other; Ar₁ and Ar₂ represent asubstituted or non-substituted fused polycyclic aromatic group in whichthe total of benzene rings is 3 or more or a fused polycyclicheterocyclic group in which the total of benzene rings and heterocyclesis 3 or more or and which is bonded to the fluorene group viasubstituted or non-substituted carbon; Ar₁ and Ar₂ may be the same ordifferent; and n represents an integer of 1 to 10.

Among the host materials described above, the anthracene derivatives arepreferred, and the monoanthracene derivatives are more preferred. Theasymmetric anthracene derivatives are particularly preferred.

Phosphorescent compounds can also be used as the luminescent material ofa dopant. Compounds containing a carbazole ring for a host material arepreferred as the phosphorescent compound. The dopant is a compound whichcan emit light from a triplet exciton, and it shall not specifically berestricted as long as light is emitted from a triplet exciton. It ispreferably a metal complex containing at least one metal selected fromthe group consisting of Ir, Ru, Pd, Pt, Os and Re, and a porphyrin metalcomplex or an ortho-metallated metal complex is preferred.

The host suited to phosphorescence comprising the compound containing acarbazole ring is a compound having a function in which transfer ofenergy from an excited state thereof to a phosphorescent compound takesplace to result in allowing the phosphorescent compound to emit light.The host compound shall not specifically be restricted as long as it isa compound which can transfer exciton energy to the phosphorescentcompound, and it can suitably be selected according to the purposes. Itmay have an optional heterocycle in addition to a carbazole ring.

The specific examples of the above host compound include carbazolederivatives, triazole derivatives, oxazole derivatives, oxadiazolederivatives, imidazole derivatives, polyarylalkane derivatives,pyrazoline derivatives, pyrazolone derivatives, phenylenediaminederivatives, arylamine derivatives, amino-substituted chalconederivatives, styrylanthracene derivatives, fluorenone derivatives,hydrazone derivatives, stilbene derivatives, silazane derivatives,aromatic tertiary amine compounds, styrylamine compounds, aromaticdimethylidene base compounds, porphyrin base compounds,anthraquinonedimethane derivatives, anthrone derivatives,diphenylquinone derivatives, thiopyran dioxide derivatives, carbodiimidederivatives, fluorenilidenemethane derivatives, distyrylpyrazinederivatives, heterocyclic tetracarboxylic anhydride such asnaphthaleneperylene, metal complexes of phthalocyanine derivatives and8-quinolinol derivatives, various metal complex polysilane basecompounds represented by metal complexes comprising metalphthalocyanine, benzoxazole and benzothiazole as ligands andmacromolecule compounds including poly(N-vinylcarbazole) derivatives,aniline base copolymers, thiophene oligomers, electroconductive highmolecular oligomers such as polythiophene, polythiophene derivatives,polyphenylene derivatives, polyphenylenevinylene derivatives andpolyfluorene derivatives. The host compounds may be used alone or incombination two or more kinds thereof.

The specific examples thereof include the following compounds:

The phosphorescent dopant is a compound which can emit light from atriplet exciton. It shall not specifically be restricted as long aslight is emitted from a triplet exciton. It is preferably a metalcomplex containing at least one metal selected from the group consistingof Ir, Ru, Pd, Pt, Os and Re, and a porphyrin metal complex or anortho-metallated metal complex is preferred. The porphyrin metal complexis preferably a porphyrin platinum complex. The phosphorescent compoundsmay be used alone or in combination of two or more kinds thereof.

A ligand forming the ortho-metallated metal complex includes variousones, and the preferred ligand includes 2-phenylpyridine derivatives,7,8-benzoquinoline derivatives, 2-(2-thienyl)pyridine derivatives,2-(1-naphthyl)pyridine derivatives, 2-phenylquinoline derivatives andthe like. The above derivatives may have, if necessary, substituents. Inparticular, the compounds into which fluorides and trifluoromethyl areintroduced are preferred as a blue color dopant. Further, it may have,as an auxiliary ligand, ligands other than the ligands described abovesuch as acetylacetonate, picric acid and the like.

A content of the phosphorescent dopant in the light emitting layer shallnot specifically be restricted, and it can suitably be selectedaccording to the purposes. It is, for example, 0.1 to 70 mass %,preferably 1 to 30 mass %. If a content of the phosphorescent dopant isless than 0.1 mass %, light emission is faint, and an addition effectthereof is not sufficiently exhibited. On the other hand, if it exceeds70 mass %, a phenomenon called concentration quenching becomes marked,and the device performance is reduced.

The light emitting layer may contain, if necessary, a hole transportingmaterial, an electron transporting material and a polymer binder.

Further, a film thickness of the light emitting layer is preferably 5 to50 nm, more preferably 7 to 50 nm and most preferably 10 to 50 nm. If itis less than 5 nm, it is difficult to form the light emitting layer, andcontrolling of the chromaticity is likely to become difficult. On theother hand, if it exceeds 50 nm, the driving voltage is likely to go up.

(5) Hole Injecting and Transporting Layers (Hole Transporting Zone)

The hole injecting and transporting layers are layers for assistinginjection of a hole into the light emitting layer to transport it to thelight emitting region, and they have a large hole mobility and show asmall ionization energy of usually 5.5 eV or less. A material whichtransports a hole to the light emitting layer by a lower electric fieldstrength is preferred as the above hole injecting and transportinglayers, and more preferred is a material in which a mobility of a holeis at least 10⁻⁴ cm²/V·second in applying an electric field of, forexample, 10⁴ to 10⁶ V/cm.

When the aromatic amine derivative of the present invention is used inthe hole transporting zone, the hole injecting and transporting layersmay be formed from the aromatic amine derivative of the presentinvention alone or it may be used in a mixture with other materials.

The materials for forming the hole injecting and transporting layers bymixing with the aromatic amine derivative of the present invention shallnot specifically be restricted as long as they have the preferredproperties described above, and capable of being used are optionalmaterials selected from materials which have so far conventionally beenused as charge transporting materials of holes in photoconductivematerials and publicly known materials which are used for hole injectingand transporting layers in an organic EL device.

The specific examples thereof include triazole derivatives (refer toU.S. Pat. No. 3,112,197 and the like), oxadiazole derivatives (refer toU.S. Pat. No. 3,189,447 and the like), imidazole derivatives (refer toJapanese Patent Publication No. 16096/1962 and the like), polyarylalkanederivatives (refer to U.S. Pat. No. 3,615,402, ditto U.S. Pat. No.3,820,989 and ditto U.S. Pat. No. 3,542,544, Japanese Patent PublicationNo. 555/1970 and ditto 10983/1976 and Japanese Patent ApplicationLaid-Open No. 93224/1976, ditto 17105/1980, ditto 4148/1981, ditto10866/1980, ditto 156953/1980 and ditto 36656/1981 and the like),pyrazoline derivatives and pyrazolone derivatives (refer to U.S. Pat.No. 3,180,729 and ditto U.S. Pat. No. 4,278,746 and Japanese PatentApplication Laid-Open No. 88064/1980, ditto 88065/1980, ditto105537/1974, ditto 51086/1980, ditto 80051/1981, ditto 88141/1981, ditto45545/1982, ditto 112637/1979 and ditto 74546/1980 and the like),phenylenediamine derivatives (refer to U.S. Pat. No. 3,615,404, JapanesePatent Publication No. 10105/1976, ditto 3712/1971 and ditto 25336/1972and Japanese Patent Application Laid-Open No. 53435/1979, ditto110536/1979 and ditto 119925/1979 and the like), arylamine derivatives(refer to U.S. Pat. No. 3,567,450, ditto U.S. Pat. No. 3,180,703, dittoU.S. Pat. No. 3,240,597, ditto U.S. Pat. No. 3,658,520, ditto U.S. Pat.No. 4,232,103, ditto U.S. Pat. No. 4,175,961 and ditto U.S. Pat. No.4,012,376, Japanese Patent Publication No. 35702/1974 and ditto27577/1964, Japanese Patent Application Laid-Open No. 144250/1980, ditto119132/1981 and ditto 22437/1981 and German Patent 1,110,518 and thelike), amino-substituted chalcone derivatives (refer to U.S. Pat. No.3,526,501 and the like), oxazole derivatives (disclosed in U.S. Pat. No.3,257,203 and the like), styrylanthracene derivatives (refer to JapanesePatent Application Laid-Open No. 46234/1981 and the like), fluorenonederivatives (refer to Japanese Patent Application Laid-Open No.110837/1979 and the like), hydrazone derivatives (refer to U.S. Pat. No.3,717,462, Japanese Patent Application Laid-Open No. 59143/1979, ditto52063/1980, ditto 52064/1980, ditto 46760/1980, ditto 85495/1980, ditto11350/1982 and ditto 148749/1982, Japanese Patent Application Laid-OpenNo. 311591/1990 and the like), stilbene derivatives (Japanese PatentApplication Laid-Open No. 210363/1986, ditto 228451/1986, ditto14642/1986, ditto 72255/1986, ditto 47646/1987, ditto 36674/1987, ditto10652/1987, ditto 30255/1987, ditto 93455/1985, ditto 94462/1985, ditto174749/1985 and ditto 175052/1985 and the like), silazane derivatives(U.S. Pat. No. 4,950,950), polysilane base (Japanese Patent ApplicationLaid-Open No. 204996/1990), aniline base copolymers (Japanese PatentApplication Laid-Open No. 282263/1990) and electroconductive highmolecular oligomers (particularly thiophene oligomers) disclosed inJapanese Patent Application Laid-Open No. 211399/1989.

The compounds described above can be used as the material for the holeinjecting and transporting layers, and preferably used are porphyrincompounds (disclosed in Japanese Patent Application Laid-Open No.2956965/1988 and the like), aromatic tertiary amine compounds andstyrylamine compounds (refer to U.S. Pat. No. 4,127,412 and JapanesePatent Application Laid-Open No. 27033/1978, ditto 58445/1979, ditto149634/1979, ditto 64299/1979, ditto 79450/1980, ditto 144250/1980,ditto 119132/1981, ditto 295558/1986, ditto 98353/1986 and ditto295695/1988 and the like), and the aromatic tertiary amine compounds areparticularly preferably used.

Further, capable of being given are compounds having two fused aromaticrings in a molecule described in U.S. Pat. No. 5,061,569, for example,4,4′-bis(N-(1-naphthyl)-N-phenylamino)biphenyl (hereinafter abbreviatedas NPD) and 4,4′,4″-tris(N-(3-methylphenyl)-N-phenylamino)triphenylamine(hereinafter abbreviated as MTDATA) in which three triphenylamine unitsare combined in the form of a star burst type disclosed in JapanesePatent Application Laid-Open No. 308688/1992.

Further, inorganic compounds such as p type Si, p type SiC and the likecan also be used as the material for the hole injecting and transportinglayers in addition to the aromatic dimethylidene base compoundsdescribed above shown as the material for the light emitting layer.

In addition to the above compounds, a nitrogen-containing heterocyclicderivative represented by the following formula which is disclosed inJapanese Patent No. 3571977 can be used as well:

wherein R¹²¹ to R¹²⁶ each represent any of a substituted ornon-substituted alkyl group, a substituted or non-substituted arylgroup, a substituted or non-substituted aralkyl group and a substitutedor non-substituted heterocyclic group; provided that R¹²¹ to R¹²⁶ may bethe same or different; R¹²¹ and R¹²², R¹²² and R¹²³, R¹²³ and R¹²⁴, R¹²⁴and R¹²⁵, R¹²⁵ and R¹²⁶ and R¹²⁶ and R¹²¹ may form fused rings.

Further, a compound represented by the following formula which isdescribed in U.S. 2004/0113547 A1 can be used as well:

wherein R131 to R136 are substituents and are preferably electronattractive groups such as a cyano group, a nitro group, a sulfonylgroup, a carbonyl group, a trifluoromethyl group, halogen atoms and thelike.

As represented by the above materials, acceptor materials can also beused as the hole injecting material. The specific examples thereof havebeen described above.

Further, inorganic compounds such as p type Si, p type SiC and the likecan also be used as the material for the hole injecting layer inaddition to the aromatic dimethylidene base compounds described aboveshown as the material for the light emitting layer.

The hole injecting and transporting layers can be formed by making athin film from the aromatic amine derivative of the present invention bya publicly known method such as, for example, a vacuum vapor depositionmethod, a spin coating method, a casting method, an LB method and thelike. A film thickness of the hole injecting and transporting layersshall not specifically be restricted, and it is usually 5 nm to 5 μm.The above hole injecting and transporting layers may be constituted froma single layer comprising at least one of the materials described aboveas long as the aromatic amine derivative of the present invention iscontained in the hole transporting zone, and hole injecting andtransporting layers comprising compounds which are different from thoseused in the hole injecting and transporting layers described above maybe laminated thereon.

Further, an organic semiconductor layer may be provided as a layer forassisting injection of a hole or injection of an electron into the lightemitting layer, and the layer having a conductance of 10⁻¹⁰ S/cm or moreis suited. Capable of being used as a material for the above organicsemiconductor layer are conductive oligomers such asthiophene-containing oligomers and arylamine-containing oligomersdisclosed in Japanese Patent Application Laid-Open No. 193191/1996 andconductive dendrimers such as arylamine-containing dendrimers.

(6) Electron Injecting and Transporting Layers

The electron injecting and transporting layers are layers for assistinginjection of an electron into the light emitting layer to transport itto the light emitting region, and they have a large electron mobility.Also, the adhesion improving layer is a layer comprising particularly amaterial having a good adhesive property with the cathode in the aboveelectron injecting layer.

It is known that since light emitted in an organic EL device isreflected by an electrode (in this case, a cathode), light transmitteddirectly from an anode is interfered with light emitted via reflectionby the electrode. In order to make efficient use of the aboveinterference effect, the electron transporting layer is suitablyselected in a film thickness of several nm to several μm, andparticularly when the film thickness is large, the electron mobility ispreferably at least 10⁻⁵ cm²/Vs or more in applying an electric field of10⁴ to 10⁶ V/cm in order to avoid a rise in voltage.

The materials used for the electron injecting layer are suitably metalcomplexes of 8-hyroxyquinoline or derivatives thereof and oxadiazolederivatives. The specific examples of the metal complexes of8-hyroxyquinoline or the derivatives thereof include metal chelateoxynoid compounds containing chelates of oxine (in general, 8-quinolinolor 8-hyroxyquinoline), and, for example, tris(8-quinolinol)aluminum canbe used as the electron injecting material.

On the other hand, the oxadiazole derivative includes electrontransmitting compounds represented by the following formulas:

wherein Ar¹, Ar², Ar³, Ar⁵, Ar⁶ and Ar⁹ each represent a substituted ornon-substituted aryl group, and they may be the same as or differentfrom each other; Ar⁴, Ar⁷ and Ar⁸ each represent a substituted ornon-substituted arylene group, and they may be the same as or differentfrom each other.

In this connection, the aryl group includes, for example, phenyl,biphenyl, anthranyl, perylenyl and pyrenyl. Also, the arylene groupincludes phenylene, naphthylene, biphenylene, anthranylene, perylenyleneand pyrenylene. Substituents thereof include an alkyl group having 1 to10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms and a cyanogroup. The above electron transmitting compounds have preferably a thinfilm-forming property.

The following compounds can be given as the specific examples of theelectron transmitting compounds described above:

Further, Compounds represented by the following Formulas (A) to (F) canbe used as the materials used for the electron injecting layer and theelectron transporting layer.

Nitrogen-containing heterocyclic derivatives represented by:

(in Formulas (A) and (B), A¹ to A³ each are independently a nitrogenatom or a carbon atom; Ar¹ is a substituted or non-substituted arylgroup having 6 to 60 ring carbon atoms or a substituted ornon-substituted heteroaryl group having 3 to 60 ring carbon atoms; Ar²is a hydrogen atom, a substituted or non-substituted aryl group having 6to 60 ring carbon atoms, a substituted or non-substituted heteroarylgroup having 3 to 60 ring carbon atoms, a substituted or non-substitutedalkyl group having 1 to 20 carbon atoms or a substituted ornon-substituted alkoxy group having 1 to 20 carbon atoms or a divalentgroup thereof; provided that any one of Ar¹ and Ar² is a substituted ornon-substituted fused ring group having 10 to 60 ring carbon atoms or asubstituted or non-substituted monohetero fused ring group having 3 to60 ring carbon atoms;L₁, L₂ and L each are independently a single bond, a substituted ornon-substituted arylene group having 6 to 60 ring carbon atoms, asubstituted or non-substituted heteroarylene group having 3 to 60 ringcarbon atoms or a substituted or non-substituted fluorenylene group;R is a hydrogen atom, a substituted or non-substituted aryl group having6 to 60 ring carbon atoms, a substituted or non-substituted heteroarylgroup having 3 to 60 ring carbon atoms, a substituted or non-substitutedalkyl group having 1 to 20 carbon atoms or a substituted ornon-substituted alkoxy group having 1 to 20 carbon atoms; n is aninteger of 0 to 5; when n is 2 or more, plural R's may be the same ordifferent, and adjacent plural R's may be combined with each other toform a carbocyclic aliphatic ring or a carbocyclic aromatic ring).

Nitrogen-containing heterocyclic derivative represented by:

HAr-L-Ar¹—Ar²  (C)

(wherein HAr is a nitrogen-containing heterocycle having 3 to 40 carbonatoms which may have a substituent; L is a single bond, an arylene grouphaving 6 to 60 carbon atoms which may have a substituent, aheteroarylene group having 3 to 60 carbon atoms which may have asubstituent or a fluorenylene group which may have a substituent; Ar¹ isa divalent aromatic hydrocarbon group having 6 to 60 carbon atoms whichmay have a substituent; and Ar² is an aryl group having 6 to 60 carbonatoms which may have a substituent or a heteroaryl group having 3 to 60carbon atoms which may have a substituent).

Silacyclopentadiene derivative represented by:

(wherein X and Y each are independently a saturated or unsaturatedhydrocarbon group having 1 to 6 carbon atoms, an alkoxy group, analkenyloxy group, an alkynyloxy group, a hydroxy group, a substituted ornon-substituted aryl group, a substituted or non-substituted heterocycleor a structure in which X is combined with Y to form a saturated orunsaturated ring; R¹ to R⁴ each are independently a hydrogen atom, ahalogen atom, a substituted or non-substituted alkyl group having 1 to 6carbon atoms, an alkoxy group, an aryloxy group, a perfluoroalkyl group,a perfluoroalkoxy group, an amino group, an alkylcarbonyl group, anarylcarbonyl group, an alkoxycarbonyl group, an aryloxycarbonyl group,an azo group, an alkylcarbonyloxy group, an arylcarbonyloxy group, analkoxycarbonyloxy group, an aryloxycarbonyloxy group, a sulfinyl group,a sulfonyl group, a sulfanyl group, a silyl group, a carbamoyl group, anaryl group, a heterocyclic group, an alkenyl group, an alkynyl group, anitro group, a formyl group, a nitroso group, a formyloxy group, anisocyano group, a cyanate group, an isocyanate group, a thiocyanategroup, an isothiocyanate group, a cyano group or a structure in whichsubstituted or non-substituted rings are fused when they are adjacent).

Borane derivative represented by:

(wherein R₁ to R₈ and Z₂ each represent independently a hydrogen atom, asaturated or unsaturated hydrocarbon group, an aromatic group, aheterocyclic group, a substituted amino group, a substituted borylgroup, an alkoxy group or an aryloxy group; X, Y and Z₁ each representindependently a saturated or unsaturated hydrocarbon group, an aromaticgroup, a heterocyclic group, a substituted amino group, an alkoxy groupor an aryloxy group; substituents of Z₁ and Z₂ may be combined with eachother to form a fused ring; n represents an integer of 1 to 3, and whenn is 2 or more, Z₁'s may be different; provided that a case in which nis 1 and X, Y and R₂ are methyl and in which R₈ is a hydrogen atom or asubstituted boryl group and a case in which n is 3 and Z₁ is methyl arenot included).

[wherein Q¹ and Q² each represent independently a ligand represented bythe following Formula (G), and L represents a halogen atom, asubstituted or non-substituted alkyl group, a substituted ornon-substituted cycloalkyl group, a substituted or non-substituted arylgroup, a substituted or non-substituted heterocyclic group, —OR¹ (R¹ isa hydrogen atom, a substituted or non-substituted alkyl group, asubstituted or non-substituted cycloalkyl group, a substituted ornon-substituted aryl group or a substituted or non-substitutedheterocyclic group) or a ligand represented by —O—Ga-Q³(Q⁴) (Q³ and Q⁴are the same as Q¹ and Q²)]:

[wherein rings A¹ and A² are a six-membered aryl ring structure whichmay have a substituent and in which they are fused with each other].

The above metal complex has a strong property of an n type semiconductorand a large electron injecting ability. Further, since it has lowproduction energy in forming the complex, a bonding property between themetal and the ligand in the metal complex formed becomes firm, and afluorescence quantum efficiency of the luminescent material grows largeras well.

The specific examples of substituents of the rings A¹ and A² forming theligand represented by Formula (G) include a halogen atom such aschlorine, bromine, iodine and fluorine, a substituted or non-substitutedalkyl group such as methyl, ethyl, propyl, butyl, s-butyl, t-butyl,pentyl, hexyl, heptyl, octyl, stearyl, trichloromethyl and the like, asubstituted or non-substituted aryl group such as phenyl, naphthyl,3-methylphenyl, 3-methoxyphenyl, 3-fluorophenyl,3-trichloromethylphenyl, 3-trifluoromethylphenyl, 3-nitrophenyl and thelike, a substituted or non-substituted alkoxy group such as methoxy,n-butoxy, t-butoxy, trichloromethoxy, trifluoroethoxy,pentafluoropropoxy, 2,2,3,3-tetrafluoropropoxy,1,1,3,3,3-hexafluoro-2-propoxy, 6-(perfluoroethyl)hexyloxy and the like,a substituted or non-substituted aryloxy group such as phenoxy,p-nitrophenoxy, p-t-butylphenoxy, 3-fluorophenoxy, pentafluorophenoxy,3-trifluoromethylphenoxy and the like, a substituted or non-substitutedalkylthio group such as methylthio, ethylthio, t-butylthio, hexylthio,octylthio trifluoromethylthio and the like, a substituted ornon-substituted arylthio group such as phenylthio, p-nitrophenylthio,p-t-butylphenylthio, 3-fluorophenylthio, pentafluorophenylthio,3-trifluoromethylphenylthio and the like, a cyano group, a nitro group,an amino group, a mono- or disubstituted amino group such asmethylamino, diethylamino, ethylamino, diethylamino, dipropylamino,dibutylamino, diphenylamino and the like, an acylamino group such asbis(acetoxymethyl)amino, bis(acetoxyethyl)amino,bis(acetoxypropyl)amino, bis(acetoxybutyl)amino and the like, a hydroxygroup, a siloxy group, an acyl group, a carbamoyl group such asmethylcarbamoyl, dimethylcarbamoyl, ethylcarbamoyl, diethylcarbamoyl,propylcarbamoyl, butylcarbamoyl, phenylcarbamoyl and the like, acarboxylic acid group, a sulfonic acid group, an imide group, acycloalkyl group such as cyclopentane, cyclohexyl and the like, an arylgroup such as phenyl, naphthyl, biphenyl, anthranyl, phenanthryl,fluorenyl, pyrenyl and the like and a heterocyclic group such aspyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, indolinyl,quinolinyl, acridinyl, pyrrolidinyl, dioxanyl, piperidinyl,morpholidinyl, piperazinyl, triatinyl, carbazolyl, furanyl, thiophenyl,oxazolyl, oxadiazolyl, benzoxazolyl, thiazolyl, thiadiazolyl,benzothiazolyl, triazolyl, imidazolyl, benzimidazolyl, puranyl and thelike. Further, the substituents described above may be combined witheach other to form six-membered aryl rings or heterocycles.

The preferred mode of the organic EL device of the present inventionincludes a device containing a reducing dopant in the region whichtransports an electron or an interfacial region between the cathode andthe organic layer. In this case, the reducing dopant is defined by asubstance which can reduce an electron transporting compound.Accordingly, various compounds can be used as long as they have areducing property of some extent, and capable of being suitably used isat least one substance selected from the group consisting of, forexample, alkali metals, alkaline earth metals, rare earth metals, oxidesof alkali metals, halides of alkali metals, oxides of alkaline earthmetals, halides of alkaline earth metals, oxides of rare earth metals orhalides of rare earth metals, organic complexes of alkali metals,organic complexes of alkaline earth metals and organic complexes of rareearth metals.

To be more specific, the preferred reducing dopant includes at least onealkali metal selected from the group consisting of Na (work function:2.36 eV), K (work function: 2.28 eV), Rb (work function: 2.16 eV) and Cs(work function: 1.95 eV) and at least one alkaline earth metal selectedfrom the group consisting of Ca (work function: 2.9 eV), Sr (workfunction: 2.0 to 2.5 eV) and Ba (work function: 2.52 eV), and thecompounds having a work function of 2.9 eV or less are particularlypreferred. Among them, the more preferred reducing dopant is at leastone alkali metal selected from the group consisting of K, Rb and Cs, andit is more preferably Rb or Cs. It is most preferably Cs. The abovealkali metals have a particularly high reducing ability, and addition ofa relatively small amount thereof to the electron injecting zone makesit possible to raise a light emitting luminance in the organic EL deviceand extend a lifetime thereof. The combination of two or more kinds ofthe above alkali metals is preferred as the reducing dopant having awork function of 2.9 eV or less, and particularly preferred is thecombination containing Cs, for example, Cs with Na, Cs with K, Cs withRb or Cs with Na and K. Containing Cs in combination makes it possibleto efficiently exhibit the reducing ability, and addition thereof to theelectron injecting zone makes it possible to enhance a light emittingluminance in the organic EL device and extend a lifetime thereof.

In the present invention, an electron injecting layer constituted froman insulator and a semiconductor may further be provided between thecathode and the organic layer. In this case, an electric current caneffectively be prevented from leaking to enhance the electron injectingproperty. Preferably used as the above insulator is at least one metalcompound selected from the group consisting of alkali metalchalcogenides, alkaline earth metal chalcogenides, halides of alkalimetals and halides of alkaline earth metals. If the electron injectinglayer is constituted from the above alkali metal chalcogenides, it ispreferred from the viewpoint that the electron injecting property canfurther be enhanced. To be specific, the preferred alkali metalchalcogenides include, for example, Li₂O, K₂O, Na₂S, Na₂Se and Na₂O, andthe preferred alkaline earth metal chalcogenides include, for example,CaO, BaO, SrO, BeO, BaS and CaSe. Also, the preferred halides of alkalimetals include, for example, LiF, NaF, KF, LiCl, KCl and NaCl. Further,the preferred halides of alkaline earth metals include, for example,fluorides such as CaF₂, BaF₂, SrF₂, MgF₂ and BeF₂ and halides other thanthe fluorides.

The semiconductor constituting the electron transporting layer includesone kind alone of oxides, nitrides or nitride oxides containing at leastone element of Ba, Ca, Sr, Yb, Al, Ga, In, Li, Na, Cd, Mg, Si, Ta, Sband Zn or combinations of two or more kinds thereof. The inorganiccompound constituting the electron transporting layer is preferably acrystallite or amorphous insulating thin film. If the electrontransporting layer is constituted from the above insulating thin film,the more homogeneous thin film is formed, and therefore picture elementdefects such as dark spots can be reduced. The above inorganic compoundincludes the alkali metal chalcogenides, the alkaline earth metalchalcogenides, the halides of alkali metals and the halides of alkalineearth metals each described above.

(7) Cathode

Substances using metals, alloys, electroconductive compounds andmixtures thereof each having a small work function (4 eV or less) forthe electrode material are used as the cathode in order to injectelectrons into the electron injecting and transporting layer or thelight emitting layer. The specific examples of the above electrodematerial include sodium, sodium.cndot.potassium alloys, magnesium,lithium, magnesium.cndot.silver alloys, aluminum/aluminum oxide,aluminum.cndot.lithium alloys, indium and rare earth metals.

The above cathode can be prepared by forming a thin film from the aboveelectrode materials by a method such as vapor deposition, sputtering andthe like.

In this respect, when light emitted from the light emitting layer istaken out from the cathode, a light transmittance of the cathode basedon light emitted is preferably larger than 10%.

A sheet resistance of the cathode is preferably several hundred Ω/□ orless, and a film thickness thereof is usually 10 nm to 1 μm, preferably50 to 200 nm.

(8) Insulating Layer

The organic EL device is liable to cause picture element defects by leakand short circuit. In order to prevent this, an insulating thin filmlayer is preferably interposed between a pair of the electrodes.

A material used for the insulating layer includes, for example, aluminumoxide, lithium fluoride, lithium oxide, cesium fluoride, cesium oxide,magnesium oxide, magnesium fluoride, calcium oxide, calcium fluoride,aluminum nitride, titanium oxide, silicon oxide, germanium oxide,silicon nitride, boron nitride, molybdenum oxide, ruthenium oxide,vanadium oxide and the like, and mixtures and laminates thereof may beused.

(9) Production Process for Organic EL Device

According to the materials and the forming methods which have been shownabove as the examples, the anode, the light emitting layer, ifnecessary, the hole injecting and transporting layer and, if necessary,the electro injecting and transporting layer are formed, and further thecathode is formed, whereby the organic EL device can be prepared. Also,the organic EL device can be prepared as well from the cathode to theanode in an order which is reverse to what was described above.

A preparation example of an organic EL device having a structure inwhich an anode/a hole injecting layer/a light emitting layer/an electroninjecting layer/a cathode are provided in order on a light transmittingsubstrate shall be described below.

First, a thin film comprising an anode material is formed on a suitablelight transmitting substrate by a method such as deposition, sputteringand the like so that a film thickness falling in a range of 1 μm orless, preferably 10 to 200 nm is obtained, whereby an anode is prepared.Next, a hole injecting layer is provided on this anode. The holeinjecting layer can be formed, as described above, by a method such as avacuum vapor deposition method, a spin coating method, a casting method,an LB method and the like, and it is formed preferably by the vacuumvapor deposition method from the viewpoints that the homogeneous film isliable to be obtained and that pinholes are less liable to be produced.When forming the hole injecting layer by the vacuum vapor depositionmethod, the depositing conditions thereof are varied according to thecompounds used (materials for the hole injecting layer), the crystalstructure of the targeted hole injecting layer and the recombinationstructure, and in general, they are suitably selected preferably in theranges of a depositing source temperature of 50 to 450° C., a vacuumdegree of 10⁻⁷ to 10⁻³ Torr, a depositing speed of 0.01 to 50 nm/second,a substrate temperature of −50 to 300° C. and a film thickness of 5 nmto 5 μm.

Next, a light emitting layer can be formed on the hole injecting layerby making a thin film from the desired organic luminescent material by amethod such as a vacuum vapor deposition method, sputtering, a spincoating method, a casting method and the like, and it is formedpreferably by the vacuum vapor deposition method from the viewpointsthat the homogeneous film is liable to be obtained and that pinholes areless liable to be produced. When forming the light emitting layer by thevacuum vapor deposition method, the depositing conditions thereof arevaried according to the compounds used, and in general, they can beselected from the same condition ranges as in the hole injecting layer.

Next, an electron injecting layer is provided on the above lightemitting layer. It is formed preferably by the vacuum vapor depositionmethod as is the case with the hole injecting layer and the lightemitting layer since the homogeneous film has to be obtained. Thedepositing conditions thereof can be selected from the same conditionranges as in the hole injecting layer and the light emitting layer.

The aromatic amine compound of the present invention can be codepositedtogether with the other materials, though varied depending on that it isadded to any layer in the light emitting zone and the hole transportingzone, when using the vacuum vapor deposition method. When using the spincoating method, it can be added by mixing with the other materials.

Lastly, a cathode is laminated, whereby an organic EL device can beobtained.

The cathode is constituted from metal, and therefore the vapordeposition method and the sputtering method can be used. However, thevacuum vapor deposition method is preferred in order to protect theorganic substance layer of the base from being damaged in making thefilm.

The above organic EL device is preferably prepared serially from theanode up to the cathode after being evacuated once.

The forming methods of the respective layers in the organic EL device ofthe present invention shall not specifically be restricted, and theforming methods carried out by the vacuum vapor deposition method andthe spin coating method which have so far publicly been known can beused. The organic thin film layer containing the compound represented byFormula (1) described above which is used for the organic EL device ofthe present invention can be formed by a publicly known method carriedout by a coating method such as a vacuum vapor deposition method, amolecular beam epitaxy method (MBE method) or, using a solution preparedby dissolving the compounds into a solvent, in accordance with a knowncoating process such as the dipping process, the spin coating process,the casting process, the bar coating process, or the roll coatingprocess.

The film thicknesses of the respective organic layers in the organic ELdevice of the present invention shall not specifically be restricted,and in general, if the film thicknesses are too small, defects such aspinholes are liable to be caused. On the other hand, if they are toolarge, high voltage has to be applied, and the efficiency isdeteriorated, so that they fall preferably in a range of several nm to 1μm.

When applying a direct voltage to the organic EL device, light emissioncan be observed by applying a voltage of 5 to 40 V setting a polarity ofthe anode to plus and that of the cathode to minus. An electric currentdoes not flow by applying a voltage at a reverse polarity, and lightemission is not caused at all. Further, when applying an AC voltage,uniform light emission can be observed only when the anode has a pluspolarity and the cathode has a minus polarity. The waveform of analternating current applied may be optional.

EXAMPLES

The present invention shall be explained in further details below withreference to synthetic examples and examples. Intermediates synthesizedin Synthetic Examples 1 to 14 have the following structures:

Synthetic Example 1 Synthesis of Intermediate 1

A three neck flask of 1000 ml was charged with 47 g of 4-bromobiphenyl,23 g of iodine, 9.4 g of periodic acid dihydrate, 42 ml of water, 360 mLof acetic acid and 11 mL of sulfuric acid under argon flow, and themixture was stirred at 65° C. for 30 minutes and then reacted at 90° C.for 6 hours. The reaction product was poured into ice and water andfiltered. The filtered matter was washed with water and then withmethanol, whereby 67 g of a white powder was obtained. The principalpeak of m/z=358 and 360 versus C₁₂H₁₅BrI=359 was obtained by analysis ofFD-MS, and therefore it was identified as the intermediate 1.

Synthetic Example 2 Synthesis of Intermediate 2

A three neck flask of 300 ml was charged with 10 g of p-terphenyl, 12 gof iodine, 4.9 g of periodic acid dihydrate, 20 mL of water, 170 mL ofacetic acid and 22 mL of sulfuric acid under argon flow, and the mixturewas stirred at 65° C. for 30 minutes and then reacted at 90° C. for 6hours. The reaction product was poured into ice and water and filtered.The filtered matter was washed with water and then with methanol,whereby 18 g of a white powder was obtained. The principal peak ofm/z=482 versus C₁₈H₁₂I₂=482 was obtained by analysis of FD-MS, andtherefore it was identified as the intermediate 2.

Synthetic Example 3 Synthesis of Intermediate 3

A three neck flask of 1000 ml was charged with 42.4 g of4-dibenzofuranboronic acid, 56.0 g of 4-iodobromobenzene, 6.9 g oftetrakis-(triphenylphosphine)palladium (Pd(PPh₃)₄), 320 mL of a sodiumcarbonate (Na₂CO₃) solution of 2M and 320 mL of toluene under argonflow, and then they were reacted at 80° C. for 8 hours. The reactionsolution was extracted with toluene/water, and the extract was dried onanhydrous sodium sulfate. This was concentrated under reduced pressure,and a crude product obtained was refined through a column, whereby 28.5g of a white powder was obtained. It was identified as the intermediate3 by analysis of FD-MS.

Synthetic Example 4 Synthesis of Intermediate 4

Reaction was carried out in the same manner, except that in SyntheticExample 3, 71 g of the intermediate 1 was used in place of4-iodobromobenzene, whereby 42.4 g of a white powder was obtained. Itwas identified as the intermediate 4 by analysis of FD-MS.

Synthetic Example 5 Synthesis of Intermediate 5

A three neck flask of 500 ml was charged with 24.9 g of2-bromodibenzofuran obtained by a synthetic method described in adocument (J. Org. Chem., 62, 5, 1997, 1348 to 1355), 80 mL of dehydratedether and 80 mL of dehydrated toluene under argon flow. 120 mmol of an-butyllithium/hexane solution was poured thereinto at −30° C. to carryout reaction at 0° C. for one hour. The reaction solution was cooleddown to −70° C., and 70 mL of triisopropyl borate (B(OiPr)₃) was pouredthereinto. The solution was heated slowly up to room temperature andstirred for one hour. The solution to which 80 mL of 10% hydrochloricacid was added was extracted with ethyl acetate/water, and then theextract was dried on anhydrous sodium sulfate. The solution wasconcentrated and washed with hexane to thereby obtain 10.4 g of aboronic acid compound.

Reaction was carried out in the same manner, except that in SyntheticExample 3, 42.4 g of 2-dibenzofuranboronic acid obtained above was usedin place of 4-dibenzofuranboronic acid, whereby 24.6 g of a white powderwas obtained. It was identified as the intermediate 5 by analysis ofFD-MS.

Synthetic Example 6 Synthesis of Intermediate 6

A flask was charged with 5.5 g of aniline, 16.2 g of the intermediate 3,6.8 g of sodium t-butoxide (manufactured by Hiroshima Wako Co., Ltd.),0.46 g of tris(dibenzylideneacetone)dipalladium (0) (manufactured byAldrich Co., Ltd.) and 300 mL of dehydrated toluene under argon flow tocarry out reaction at 80° C. for 8 hours.

After cooling down, 500 ml of water was added thereto, and the mixturewas filtered through celite. The filtrate was extracted with toluene,and the extract was dried on anhydrous magnesium sulfate. This wasconcentrated under reduced pressure, and a crude product obtained wasrefined through a column and recrystallized from toluene. It wasseparated by filtration and then dried, whereby 10.1 g of a pale yellowpowder was obtained. It was identified as the intermediate 6 by analysisof FD-MS.

Synthetic Example 7 Synthesis of Intermediate 7

A flask was charged with 10 g of the intermediate 6, 8.8 g of1-bromo-4-iodobenzene (manufactured by Aldrich Co., Ltd.), 3 g of sodiumt-butoxide (manufactured by Hiroshima Wako Co., Ltd.), 0.5 g ofbis(triphenylphosphine)palladium chloride (II) (manufactured by TokyoKasei Kogyo Co., Ltd.) and 500 ml of xylene under argon flow to carryout reaction at 130° C. for 24 hours.

After cooling down, 1000 ml of water was added thereto, and the mixturewas filtered through celite. The filtrate was extracted with toluene,and the extract was dried on anhydrous magnesium sulfate. This wasconcentrated under reduced pressure, and a crude product obtained wasrefined through a column and recrystallized from toluene. It wasseparated by filtration and then dried, whereby 3.2 g of a pale yellowpowder was obtained. It was identified as the intermediate 7 by analysisof FD-MS.

Synthetic Example 8 Synthesis of Intermediate 8

Reaction was carried out in the same manner, except that in SyntheticExample 3, 71 g of 4-bromoaniline was used in place of4-iodobromobenzene, whereby 26.4 g of a white powder was obtained. Itwas identified as the intermediate 8 by analysis of FD-MS.

Synthetic Example 9 Synthesis of Intermediate 9

Reaction was carried out in the same manner, except that in SyntheticExample 7, 5.2 g of diphenylamine was used in place of the intermediate3 and that 11.0 g of the intermediate 1 was used in place of1-bromo-4-iodobenzene, whereby 2.6 g of a white powder was obtained. Itwas identified as the intermediate 9 by analysis of FD-MS.

Synthetic Example 10 Synthesis of Intermediate 10

Reaction was carried out in the same manner, except that in SyntheticExample 6, 13.0 g of the intermediate 8 was used in place of aniline andthat 11.6 g of 4-bromobiphenyl was used in place of the intermediate 4,whereby 13.1 g of a white powder was obtained. It was identified as theintermediate 10 by analysis of FD-MS.

Synthetic Example 11 Synthesis of Intermediate 11

A flask was charged with 547 g of 1-acetamidenaphthalene (manufacturedby Tokyo Kasei Kogyo Co., Ltd.), 400 g of 4,4′-diiodobiphenyl(manufactured by Wako Pure Chemical Industries, Ltd.), 544 g ofpotassium carbonate (manufactured by Wako Pure Chemical Industries,Ltd.), 12.5 g of copper powder (manufactured by Wako Pure ChemicalIndustries, Ltd.) and 2 L of decalin under argon flow to carry outreaction at 190° C. for 4 days.

The reaction solution was cooled down after reaction, and insolublematters were obtained by filtration. The filtered matter was dissolvedin 4.5 L of toluene to remove insoluble matters, and then it wassubjected to activated carbon treatment and concentrated. Acetone 3 Lwas added thereto to obtain 382 g of deposited crystal by filtration.

This was suspended in 5 L of ethylene glycol (manufactured by Wako PureChemical Industries, Ltd.) and 50 mL of water, and 145 g of a 85%potassium hydroxide aqueous solution was added thereto, followed bycarrying out reaction at 120° C. for 2 hours.

After finishing the reaction, the reaction liquid was poured into 10 Lof water, and deposited crystal was obtained by filtration and washedwith water and methanol.

The crystal thus obtained was dissolved in 3 L of tetrahydrofuran byheating. The solution was treated with activated carbon black and thenconcentrated, and acetone was added thereto to deposit crystal. This wasseparated by filtration to obtain 264 g of a white powder. It wasidentified as the intermediate 11 by analysis of FD-MS.

Synthetic Example 12 Synthesis of Intermediate 12

A three neck flask of 200 ml was charged with 20.0 g of 4-bromobiphenyl(manufactured by Tokyo Kasei Kogyo Co., Ltd.), 8.64 g of sodiumt-butoxide (manufactured by Wako Pure Chemical Industries, Ltd.) and 84mg of palladium acetate (manufactured by Wako Pure Chemical Industries,Ltd.). Further, a stirring rod was put therein, and rubber caps were setat both sided of the flask. A Gimroth condenser for refluxing was set inthe neck of the center, and a three-way cock and a balloon charged withargon gas were set thereon to substitute the inside of the system threetimes with the argon gas in the balloon by means of a vacuum pump.

Next, 120 mL of dehydrated toluene (manufactured by Hiroshima Wako Co.,Ltd.), 4.08 mL of benzylamine (manufactured by Tokyo Kasei Kogyo Co.,Ltd.) and 338 μL of tris-t-butylphsosphine (a 2.22 mol/L toluenesolution, manufactured by Aldrich Co., Ltd.) were added thereto througha rubber septum by means of a syringe and stirred at room temperaturefor 5 minutes. Next, the flask was set on an oil bath and graduallyheated up to 120° C. while stirring the solution. After 7 hours passed,the flask was taken off from the oil bath to terminate the reaction, andit was left standing for 12 hours under argon atmosphere. The reactionsolution was transferred into a separating funnel, and 600 mL ofdichloromethane was added thereto to dissolve the precipitate. Theorganic layer was washed with 120 mL of a saturated brine and then driedon anhydrous potassium carbonate. The solvent of the organic layerobtained by filtering off potassium carbonate was distilled off, and 400mL of toluene and 80 mL of ethanol were added to the resulting residue.The flask to which a drying tube was mounted was heated to 80° C. tocompletely dissolve the residue. Then, the flask was left standing for12 hours and slowly cooled down to room temperature to thereby expediterecrystallization. Deposited crystal was separated by filtration anddried under vacuum at 60° C., whereby 13.5 g ofN,N-di-(4-biphenylyl)-benzylamine was obtained. A single neck flask of300 mL was charged with 1.35 g of N,N-di-(4-biphenylyl)-benzylamine and135 mg of palladium-activated carbon black (palladium content: 10% byweight, manufactured by Hiroshima Wako Co., Ltd.), and 100 mL ofchloroform and 20 mL of ethanol were added to dissolve it. Next, astirring rod was put in the flask, and then a three-way cock which wasequipped a balloon charged with 2 L of hydrogen gas was mounted to theflask. The inside of the flask was substituted 10 times with hydrogengas by means of a vacuum pump. Lost hydrogen gas was newly charged toset again a volume of hydrogen gas to 2 L, and then the solution wasvigorously stirred at room temperature. After stirring for 30 hours, 100mL of dichloromethane was added thereto to separate the catalyst byfiltration. Next, the solution obtained was transferred into aseparating funnel and washed with 50 mL of a sodium hydrogencarbonatesaturated aqueous solution, and then the organic layer was separated anddried on anhydrous potassium carbonate. After filtered, the solvent wasdistilled off, and 50 mL of toluene was added to the resulting residueto carry out recrystallization. Deposited crystal was separated byfiltration and dried under vacuum at 50° C., whereby 0.99 g ofdi-4-biphenylylamine was obtained.

A flask was charged with 10 g of di-4-biphenylylamine, 9.7 g of4,4′-dibromobiphenyl (manufactured by Tokyo Kasei Kogyo Co., Ltd.), 3 gof sodium t-butoxide (manufactured by Hiroshima Wako Co., Ltd.), 0.5 gof bis(triphenylphosphine)palladium chloride (II) (manufactured by TokyoKasei Kogyo Co., Ltd.) and 500 ml of xylene under argon flow to carryout reaction at 130° C. for 24 hours. After cooling down, 1000 ml ofwater was added thereto, and the mixture was filtered through celite.The filtrate was extracted with toluene, and the extract was dried onanhydrous magnesium sulfate. This was concentrated under reducedpressure, and a crude product obtained was refined through a column andrecrystallized from toluene. It was separated by filtration and thendried, whereby 9.1 g of 4′-bromo-N,N-dibiphenylyl-4-amino-1,1′-biphenyl(intermediate 12).

Synthetic Example 13 Synthesis of Intermediate 13

Reaction was carried out in the same manner, except that in SyntheticExample 10, 8.0 g of 1-bromonaphthalene was used in place of4-bromobiphenyl, whereby 9.6 g of a white powder was obtained. It wasidentified as the intermediate 13 by analysis of FD-MS.

Synthetic Example 14 Synthesis of Intermediate 14

Reaction was carried out in the same manner, except that in SyntheticExample 10, 16.1 g of the intermediate 3 was used in place of4-bromobiphenyl, whereby 10.5 g of a white powder was obtained. It wasidentified as the intermediate 14 by analysis of FD-MS.

Compounds H1 to 15 which are the aromatic amine derivatives of thepresent invention synthesized in the following Synthetic PracticalExamples 1 to 15 and a comparative compound 1 used in ComparativeExample 1 have the following structures:

Synthetic Practical Example 1 Synthesis of Compound H1

A flask was charged with 3.4 g of N,N′-diphenylbenzidine, 6.8 g of theintermediate 3, 2.6 g of sodium t-butoxide (manufactured by HiroshimaWako Co., Ltd.), 92 mg of tris(dibenzylideneacetone)-dipalladium (O)(manufactured by Aldrich Co., Ltd.), 42 mg of tri-t-butylphosphine and100 mL of dehydrated toluene under argon flow to carry out reaction at80° C. for 8 hours.

After cooling down, 500 mL of water was added thereto, and the mixturewas filtered through celite. The filtrate was extracted with toluene,and the extract was dried on anhydrous magnesium sulfate. This wasconcentrated under reduced pressure, and a crude product obtained wasrefined through a column and recrystallized from toluene. It wasseparated by filtration and then dried, whereby 4.1 g of a pale yellowpowder was obtained. It was identified as the compound H1 by analysis ofFD-MS (field desorption mass spectrum).

Synthetic Practical Example 2 Synthesis of Compound H2

A flask was charged with 4.1 g of 4,4′-diiodobiphenyl, 7.0 g of theintermediate 8, 2.6 g of sodium t-butoxide (manufactured by HiroshimaWako Co., Ltd.), 92 mg of tris(dibenzylideneacetone)-dipalladium (O)(manufactured by Aldrich Co., Ltd.), 42 mg of tri-t-butylphosphine and100 mL of dehydrated toluene under argon flow to carry out reaction at80° C. for 8 hours.

After cooling down, 500 mL of water was added thereto, and the mixturewas filtered through celite. The filtrate was extracted with toluene,and the extract was dried on anhydrous magnesium sulfate. This wasconcentrated under reduced pressure, and a crude product obtained wasrefined through a column and recrystallized from toluene. It wasseparated by filtration and then dried, whereby 4.9 g of a pale yellowpowder was obtained. It was identified as the compound H2 by analysis ofFD-MS (field desorption mass spectrum).

Synthetic Practical Example 3 Synthesis of Compound H3

Reaction was carried out in the same manner, except that in SyntheticPractical Example 1, 4.4 g of the intermediate 11 was used in place ofN,N-diphenylbenzidine, whereby 5.2 g of a pale yellow powder wasobtained. It was identified as the compound H3 by analysis of FD-MS.

Synthetic Practical Example 4 Synthesis of Compound H4

Reaction was carried out in the same manner, except that in SyntheticPractical Example 1, 8.4 g of the intermediate 4 was used in place ofthe intermediate 3, whereby 4.6 g of a pale yellow powder was obtained.It was identified as the compound H4 by analysis of FD-MS.

Synthetic Practical Example 5 Synthesis of Compound H5

Reaction was carried out in the same manner, except that in SyntheticPractical Example 1, 6.8 g of the intermediate 5 was used in place ofthe intermediate 3, whereby 3.9 g of a pale yellow powder was obtained.It was identified as the compound H5 by analysis of FD-MS.

Synthetic Practical Example 6 Synthesis of Compound H6

A flask was charged with 8.2 g of the intermediate 10, 11.0 g of theintermediate 12, 2.6 g of sodium t-butoxide (manufactured by HiroshimaWako Co., Ltd.), 92 mg of tris(dibenzylideneacetone)-dipalladium (O)(manufactured by Aldrich Co., Ltd.), 42 mg of tri-t-butylphosphine and100 mL of dehydrated toluene under argon flow to carry out reaction at80° C. for 8 hours.

After cooling down, 500 mL of water was added thereto, and the mixturewas filtered through celite. The filtrate was extracted with toluene,and the extract was dried on anhydrous magnesium sulfate. This wasconcentrated under reduced pressure, and a crude product obtained wasrefined through a column and recrystallized from toluene. It wasseparated by filtration and then dried, whereby 13.1 g of a pale yellowpowder was obtained. It was identified as the compound H6 by analysis ofFD-MS (field desorption mass spectrum).

Synthetic Practical Example 7 (Synthesis of Compound H7)

Reaction was carried out in the same manner, except that in SyntheticPractical Example 6, 6.5 g of the intermediate 6 was used in place ofthe intermediate 10, whereby 8.2 g of a pale yellow powder was obtained.It was identified as the compound H7 by analysis of FD-MS.

Synthetic Practical Example 8 Synthesis of Compound H8

Reaction was carried out in the same manner, except that in SyntheticPractical Example 6, 7.7 g of the intermediate 13 was used in place ofthe intermediate 10, whereby 10.2 g of a pale yellow powder wasobtained. It was identified as the compound H8 by analysis of FD-MS.

Synthetic Practical Example 9 Synthesis of Compound H9

Reaction was carried out in the same manner, except that in SyntheticPractical Example 6, 10.3 g of the intermediate 14 was used in place ofthe intermediate 10, whereby 15.1 g of a pale yellow powder wasobtained. It was identified as the compound H9 by analysis of FD-MS.

Synthetic Practical Example 10 Synthesis of Compound H10

Reaction was carried out in the same manner, except that in SyntheticPractical Example 2, 4.8 g of dibromoterphenyl was used in place of4,4′-diiodobiphenyl and that 7.0 g of the intermediate 6 was used inplace of the intermediate 10, whereby 4.8 g of a pale yellow powder wasobtained. It was identified as the compound H10 by analysis of FD-MS.

Synthetic Practical Example 11 Synthesis of Compound H11

Reaction was carried out in the same manner, except that in SyntheticPractical Example 2, 3.3 g of 1,4-diiodobenzene was used in place of4,4′-diiodobiphenyl, whereby 4.1 g of a pale yellow powder was obtained.It was identified as the compound H11 by analysis of FD-MS.

Synthetic Practical Example 12 Synthesis of Compound H12

Reaction was carried out in the same manner, except that in SyntheticPractical Example 1, 2.6 g of the intermediate 10 was used in place ofN,N′-diphenylbenzidine and that 8.4 g of the intermediate 9 was used inplace of the intermediate 3, whereby 5.9 g of a pale yellow powder wasobtained. It was identified as the compound H12 by analysis of FD-MS.

Synthetic Practical Example 13 Synthesis of Compound H13

Reaction was carried out in the same manner, except that in SyntheticPractical Example 1, 10.3 g of the intermediate 7 was used in place ofthe intermediate 3, whereby 6.5 g of a pale yellow powder was obtained.It was identified as the compound H13 by analysis of FD-MS.

Synthetic Practical Example 14 Synthesis of Compound H14

A three neck flask of 300 ml was charged with 6.3 g of4-dibenzofuranboronic acid, 4.8 g of 4,4′,4″-tribromotriphenylamine, 104mg of tetrakis-(triphenylphosphine)palladium (Pd(PPh₃)₄), 48 mL of asodium carbonate (Na₂CO₃) solution of 2M and 48 mL of toluene underargon flow, and then they were reacted at 80° C. for 8 hours. Thereaction liquid was extracted with toluene/water, and the extract wasdried on anhydrous sodium sulfate. This was concentrated under reducedpressure, and a crude product obtained was refined through a column,whereby 3.9 g of a whitish yellow powder was obtained. It was identifiedas the compound H14 by analysis of FD-MS.

Synthetic Practical Example 15 Synthesis of Compound H15

Reaction was carried out in the same manner, except that in SyntheticPractical Example 10, 6.8 g of 4-dibenzothiopheneboronic acid was usedin place of 4-dibenzofuranboronic acid and that 5.1 g ofN,N′-diphenylbenzidine was used in place of4,4′,4″-tribromotriphenylamine, whereby 7.2 g of a pale yellow powderwas obtained. It was identified as the compound H15 by analysis ofFD-MS.

Example 1 Production of Organic EL Device

A glass substrate (manufactured by Geomatech Co., Ltd.) of 25 mm×75mm×1.1 mm thickness equipped with an ITO transparent electrode wassubjected to supersonic wave washing in isopropyl alcohol for 5 minutesand then to UV ozone washing for 30 minutes.

After washed, the glass substrate equipped with an ITO transparentelectrode line was loaded in a substrate holder of a vacuum vapordeposition apparatus, and a film of a compound H232 shown below having afilm thickness of 60 nm was formed on a face of a side at which thetransparent electrode line was formed so that it covered the transparentelectrode described above. This H232 film functions as a hole injectinglayer. A film of the compound H1 described above having a film thicknessof 20 nm was formed as a hole transporting material on the above H232film. This film functions as a hole transporting layer. Further, acompound EM1 shown below was deposited thereon to form a film having afilm thickness of 40 nm. At the same time, the following amine compoundD1 having a styryl group was deposited as a light emitting molecule sothat a weight ratio of EM1 to D1 was 40:2. This film functions as alight emitting layer.

A film of Alq shown below having a film thickness of 10 nm was formed onthe above film. This film functions as an electron injecting layer.Then, Li (Li source: manufactured by Saesgetter Co., Ltd.) which was areducing dopant and Alq shown below were subjected to binary vapordeposition to form an Alq:Li film (film thickness: 10 nm) as an electroninjecting layer (cathode). Metal Al was deposited on the above Alq:Lifilm to form a metal cathode, whereby an organic EL device was formed.

Further, the organic EL device thus obtained was measured for a currentefficiency and observed for a luminescent color. The luminance wasmeasured by means of CS1000 manufactured by Konica Minolta Co., Ltd. tocalculate the current efficiency at 10 mA/cm². Further, the halflifetime thereof in light emission was measured at an initial luminanceof 5000 cd/m² and room temperature in operating at a DC constantelectric current, and the results thereof are shown in Table 1.

Examples 2 to 9 Production of Organic EL Devices

Organic EL devices were prepared in the same manner, except that inExample 1, compounds described in Table 1 were used as hole transportingmaterials in place of the compound H1.

The organic EL devices thus obtained were measured for a currentefficiency and observed for a luminescent color. Further, the halflifetimes thereof in light emission were measured at an initialluminance of 5000 cd/m² and room temperature in operating at a DCconstant electric current, and the results thereof are shown in Table 1.

Comparative Example 1

An organic EL device was prepared in the same manner, except that inExample 1, a comparative compound 1 (Comparative Example 1) was used asa hole transporting material in place of the compound H1. Thecomparative compound 1 was crystallized in vapor deposition, and anormal device could not be prepared.

The organic EL device obtained was measured for a current efficiency andobserved for a luminescent color, and the half lifetime thereof in lightemission was measured at an initial luminance of 5000 cd/m² and roomtemperature in operating at a DC constant electric current, and theresults thereof are shown in Table 1.

TABLE 1 Hole Current Half transporting efficiency Luminescent lifetimematerial (cd/A) color (hour) Example 1 H1 5.1 blue 440 Example 2 H2 5.1blue 420 Example 3 H3 4.9 blue 370 Example 4 H4 5.0 blue 410 Example 5H5 4.8 blue 400 Example 6 H6 5.0 blue 420 Example 7 H7 5.1 blue 440Example 8 H8 4.8 blue 380 Example 9 H9 5.1 blue 410 ComparativeComparative 5.1 blue 280 Example 1 compound 1

Example 10 Production of Organic EL Device

An organic EL device was prepared in the same manner, except that inExample 1, the following compound D2 having a styryl group was used inplace of the amine compound D1. Me represents methyl.

The organic EL device thus obtained was measured for a currentefficiency to find that it was 4.9 cd/A and that a luminescent color wasblue. Further, the half lifetime thereof in light emission was measuredat an initial luminance of 5000 cd/m² and room temperature in operatingat a DC constant electric current to find that it was 430 hours.

Comparative Example 2

An organic EL device was prepared in the same manner, except that inExample 10, the comparative compound 1 described above was used as ahole transporting material in place of the compound H1.

The organic EL device thus obtained was measured for a currentefficiency to find that it was 4.9 cd/A and that a luminescent color wasblue. Further, the half lifetime thereof in light emission was measuredat an initial luminance of 5000 cd/m² and room temperature in operatingat a DC constant electric current to find that it was 260 hours.

Example 11 Production of Organic EL Element

An organic EL device was prepared in the same manner, except that inExample 1, H1 was used in place of H232 and that the comparativecompound 1 described above was used in place of H1.

The organic EL device thus obtained was measured for a currentefficiency to find that it was 5.1 cd/A and that a luminescent color wasblue. Further, the half lifetime thereof in light emission was measuredat an initial luminance of 5000 cd/m² and room temperature in operatingat a DC constant electric current to find that it was 360 hours.

INDUSTRIAL APPLICABILITY

As explained above in details, the aromatic amine derivative of thepresent invention is less liable to be crystallized in molecules, andaddition thereof to the organic thin film layer enhances a yield inproducing the organic EL device and makes it possible to materialize theorganic EL device having a long lifetime.

1. (canceled)
 2. An aromatic amine compound represented by Formula (5):

wherein at least one of Ar₇ to Ar₉ is represented by the followingFormula (3):

wherein R₄ is a hydrogen atom, non-substituted aryl group having 5 to 50ring carbon atoms, a substituted aryl group having 5 to 50 ring carbonatoms which said substituted aryl group is substituted by an alkyl grouphaving 1 to 4 carbon atoms, a substituted or non-substituted alkyl grouphaving 1 to 50 carbon atoms, a substituted or non-substituted alkoxygroup having 1 to 50 carbon atoms, a substituted or non-substitutedaralkyl group having 6 to 50 carbon atoms, a substituted ornon-substituted aryloxy group having 5 to 50 ring carbon atoms, asubstituted or non-substituted arylthio group having 5 to 50 ring carbonatoms, a substituted or non-substituted alkoxycarbonyl group having 2 to50 carbon atoms, a halogen atom, a cyano group, a nitro group, ahydroxyl group or a carboxyl group; R₅ and R₆ each are independently ahydrogen atom, an unsubstituted aryl group having 5 to 50 ring carbonatoms, an aryl group having 5 to 50 ring carbon atoms that issubstituted with an alkyl group having 1 to 4 carbon atoms, asubstituted or unsubstituted alkyl group having 1 to 50 carbon atoms, asubstituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, asubstituted or unsubstituted aralkyl group having 6 to 50 carbon atoms,a substituted or unsubstituted aryloxy group having 5 to 50 ring carbonatoms, a substituted or unsubstituted arylthio group having 5 to 50 ringcarbon atoms, a substituted or unsubstituted alkoxycarbonyl group having2 to 50 carbon atoms, an amino group substituted with a substituted orunsubstituted aryl group having 5 to 50 ring carbon atoms, a halogenatom, a cyano group, a nitro group, a hydroxyl group or a carboxylgroup; X is an oxygen atom; f and h each are an integer of 0 to 4; g isan integer of 0 to 3; and i is an integer of 1 to 3; plural R₄ or R₅ orR₆ may be combined with each other to form a cyclic structure of asaturated or unsaturated five-membered ring or six-membered ring whichmay be substituted; when i is 2 or more and h is not 0, plural R₆ may becombined with each other to form a cyclic structure of a saturated orunsaturated five-membered ring or six-membered ring which may besubstituted); in Formula (5), among Ar₇ to Ar₉, the groups which are notrepresented by Formula (3) each are independently a substituted orunsubstituted aryl group having 5 to 50 ring carbon atoms.
 3. Thearomatic amine compound of claim 2, wherein among Ar₇ to Ar₉, the groupswhich are not represented by Formula (3) each are independently anunsubstituted aryl group having 5 to 50 ring carbon atoms.
 4. Thearomatic amine compound of claim 2, wherein f, g, and h are
 0. 5. Thearomatic amine compound of claim 2, wherein R₄ is a hydrogen atom, anunsubstituted aryl group having 5 to 50 ring carbon atoms, an aryl grouphaving 5 to 50 ring carbon atoms that is substituted by an alkyl grouphaving 1 to 4 carbon atoms, an unsubstituted alkyl group having 1 to 50carbon atoms, an unsubstituted alkoxy group having 1 to 50 carbon atoms,an unsubstituted aralkyl group having 6 to 50 carbon atoms, anunsubstituted aryloxy group having 5 to 50 ring carbon atoms, anunsubstituted arylthio group having 5 to 50 ring carbon atoms, anunsubstituted alkoxycarbonyl group having 2 to 50 carbon atoms, ahalogen atom, a cyano group, a nitro group, a hydroxyl group or acarboxyl group; R₅ and R₆ each are independently a hydrogen atom, anunsubstituted aryl group having 5 to 50 ring carbon atoms, an aryl grouphaving 5 to 50 ring carbon atoms that is substituted by an alkyl grouphaving 1 to 4 carbon atoms, an substituted alkyl group having 1 to 50carbon atoms, an substituted alkoxy group having 1 to 50 carbon atoms,an substituted aralkyl group having 6 to 50 carbon atoms, anunsubstituted aryloxy group having 5 to 50 ring carbon atoms, anunsubstituted arylthio group having 5 to 50 ring carbon atoms, anunsubstituted alkoxycarbonyl group having 2 to 50 carbon atoms, an aminogroup substituted with an unsubstituted aryl group having 5 to 50 ringcarbon atoms, a halogen atom, a cyano group, a nitro group, a hydroxylgroup or a carboxyl group; plural R₄ or R₅ or R₆ may be combined witheach other to form a cyclic structure of a saturated or unsaturatedfive-membered ring or six-membered ring; when i is 2 or 3 and h is not0, plural R₆ may be combined with each other to form a cyclic structureof a saturated or unsaturated five-membered ring or six-membered ring;in Formula (5), among Ar₇ to Ar₉, the groups which are not representedby Formula (3) each are independently an substituted aryl group having 5to 50 ring carbon atoms.
 6. The aromatic amine compound of claim 2,wherein among Ar₇ to Ar₉, the groups which are not represented byFormula (3) are independently selected from the group consisting of aphenyl group, a naphtyl group, a biphenylyl group, an anthranyl group, aphenanthryl group, a pyrenyl group, a chrysenyl group, a fluoranthenylgroup and a fluorenyl group, each being optionally substituted.
 7. Thearomatic amine compound of claim 2, wherein among Ar₇ to Ar₉, the groupswhich are not represented by Formula (3) are independently selected fromthe group consisting of a phenyl group, a biphenylyl group, aterphenylyl group, and a 9,9-dimethyl fluorenyl group, each beingoptionally substituted.
 8. The aromatic amine compound of claim 2,wherein among Ar₇ to Ar₉, the groups which are not represented byFormula (3) are independently selected from the group consisting of aphenyl group, a naphtyl group, and a biphenylyl group, each beingoptionally substituted.
 9. The aromatic amine compound of claim 2,wherein among Ar₇ to Ar₉, the groups which are not represented byFormula (3) are independently selected from the group consisting of anunsubstituted phenyl group, an unsubstituted biphenylyl group, anunsubstituted terphenylyl group, and an unsubstituted 9,9-dimethylfluorenyl group.
 10. The aromatic amine compound of claim 2, wherein Ar₇is represented by Formula (3), Ar₈ is selected from the group consistingof a phenyl group, a biphenylyl group, a terphenylyl group, and a9,9-dimethyl fluorenyl group, each being optionally substituted, and Ar₉is selected from the group consisting of a biphenylyl group, aterphenylyl group, and a 9,9-dimethyl fluorenyl group, each beingoptionally substituted.
 11. The aromatic amine compound of claim 2,wherein Ar₇ is represented by Formula (3), Ar₈ is selected from thegroup consisting of an unsubstituted phenyl group, an unsubstitutedbiphenylyl group, an unsubstituted terphenylyl group, and anunsubstituted 9,9-dimethyl fluorenyl group, and Ar₉ is selected from thegroup consisting of an unsubstituted biphenylyl group, an unsubstitutedterphenylyl group, and an unsubstituted 9,9-dimethyl fluorenyl group.12. The aromatic amine compound of claim 2, wherein when i is 2, pluralR₆ are combined with each other to form a cyclic structure of asaturated or unsaturated five-membered ring, which may be substituted.13. The aromatic amine compound of claim 2, which is suitable for anorganic electroluminescence device.
 14. The aromatic amine compound ofclaim 2, which suitable as a hole injecting material or a holetransporting material in an organic electroluminescence device.
 15. Anorganic electroluminescence device, comprising an organic thin layercomprising a single layer or plural layers including at least a lightemitting layer interposed between a cathode and an anode, wherein atleast one layer of the organic thin layer comprises the aromatic aminecompound of claim
 2. 16. The organic electroluminescence device of claim15, wherein the organic thin layer comprises a hole injecting layer or ahole transporting layer, and the aromatic amine is in the hole injectinglayer or hole transporting layer.
 17. The organic electroluminescencedevice as described in claim 15, wherein the light emitting layercomprises styrylamine, arylamine, or a combination thereof.
 18. Theorganic electroluminescence device of claim 15, which emits blue light.19. An organic electroluminescence device, comprising an organic thinlayer comprising a single layer or plural layers including at least alight emitting layer interposed between a cathode and an anode, whereinat least one layer of the organic thin layer comprises the aromaticamine compound of claim
 6. 20. An organic electroluminescence device,comprising an organic thin layer comprising a single layer or plurallayers including at least a light emitting layer interposed between acathode and an anode, wherein at least one layer of the organic thinlayer comprises the aromatic amine compound of claim
 7. 21. An organicelectroluminescence device, comprising an organic thin layer comprisinga single layer or plural layers including at least a light emittinglayer interposed between a cathode and an anode, wherein at least onelayer of the organic thin layer contains the aromatic amine compound ofclaim
 8. 22. An organic electroluminescence device, comprising anorganic thin layer comprising a single layer or plural layers includingat least a light emitting layer interposed between a cathode and ananode, wherein at least one layer of the organic thin layer contains thearomatic amine compound of claim
 9. 23. An organic electroluminescencedevice, comprising an organic thin layer comprising a single layer orplural layers including at least a light emitting layer interposedbetween a cathode and an anode, wherein at least one layer of theorganic thin layer contains the aromatic amine compound of claim
 10. 24.An organic electroluminescence device, comprising an organic thin layercomprising a single layer or plural layers including at least a lightemitting layer interposed between a cathode and an anode, wherein atleast one layer of the organic thin layer contains the aromatic aminecompound of claim 11.